Skip to main content
NCBI home page
Precision Chemistry logoLink to Precision Chemistry
. 2025 Nov 14;4(3):219–228. doi: 10.1021/prechem.5c00098

Divergent Synthesis of Homoallylic and Allenic Sulfides, Selenides, and S,C-Sulfonium Ylides by Ruthenium Catalysis

Zhiyue He †,‡,⊥, Li Wu ‡, Yanli Ma ‡,§, Liting Wen ‡,∥, Xueqing Liu ‡,∥, Wenqian Ding ‡,∥, Wanqi Hu ‡,§, Xiaowei Wu †,‡,§,⊥,*
PMCID: PMC13014341  PMID: 41890406

Abstract

Compounds bearing benzothiophene and thioether motifs have attracted broad interest because of their prevalence across natural products, advanced materials, agrochemicals, and therapeutic agents. Importantly, many marketed drugs incorporate C–S linkages, underscoring the ongoing need for streamlined methods to construct sulfur-containing molecules. We herein report ruthenium-catalyzed divergent synthesis of homoallylic and allenic sulfides, selenides, and S,C-sulfonium ylides from iodonium ylides. This work features a ruthenium-catalyzed Doyle–Kirmse-type reaction of iodonium ylides, followed by a rare decarbonylation to deliver homoallylic and allenic sulfides/selenides. The method operates under mild conditions with broad substrate scope and good functional group tolerance, while extending the Doyle–Kirmse reaction beyond diazo compounds by employing stable, nonexplosive iodonium ylides. Furthermore, we also describe a ruthenium-catalyzed transylidation strategy that couples N-acyl sulfenamides with iodonium ylides to generate a wide range of S,C-sulfonium ylides under mild conditions. This method features a broad substrate scope, good tolerance toward functional groups, and an inexpensive ruthenium catalyst. Moreover, scale-up and subsequent derivatization experiments demonstrate its practicality. Overall, this protocol provides a versatile entry to diverse sulfonium ylides and opens opportunities for their application in synthetic chemistry.

Keywords: ruthenium catalysis; decarbonylation; [2,3]-sigmatropic rearrangement; hypervalent iodine reagents; sulfonium ylides

graphic file with name pc5c00098_0010.jpg

graphic file with name pc5c00098_0008.jpg

Introduction

Transition metal-catalyzed carbene transfer reactions have emerged as powerful tools for C–X bond formation and molecular skeleton reorganization. − Among these, the Doyle–Kirmse reaction involving diazo compounds and allylic sulfides was originally reported by Kirmse and later refined by Doyle (Figure a). − In situ generation of metal carbenes is typically achieved through transition metal-catalyzed activation of diazo compounds. , Extensive studies have since demonstrated the effectiveness of copper- and rhodium-based catalysts in facilitating this transformation, while more recently, palladium, ruthenium, cobalt, iron, gold, and silver have also been explored as viable catalysts. − In addition, several examples of metal-catalyzed Doyle–Kirmse reactions by using N-sulfonylhydrazones as diazo precursors have been reported in recent years. − The Doyle–Kirmse reaction proceeds via a metal carbene-mediated process involving sulfonium ylide formation and a subsequent [2,3]-sigmatropic rearrangement, making it a valuable strategy for constructing C–C, C–S, and C–Se bonds. This reaction provides an efficient route to homoallylic sulfides, which serve as versatile intermediates in organic synthesis. ,, In the Doyle–Kirmse reactions, diazo compounds have traditionally served as carbene precursors. Nevertheless, the instability, toxicity, and potential explosiveness of diazo compounds pose prominent safety concerns. Therefore, the development of novel, safer carbene precursors as alternatives to diazo compounds in the Doyle–Kirmse reactions is highly desirable.

1.

1

Open in a new tab

Transition metal-catalyzed Doyle–Kirmse and transylidation reactions.

Furthermore, benzothiophene, thioethers, and related derivatives have drawn significant attention owing to their broad distribution in medicinal agents, materials, and natural products. A lot of marketed pharmaceuticals feature C–S linkages, underscoring the importance of creating reliable methods for assembling sulfur-containing structures. Within this framework, sulfonium ylides serve as powerful intermediates, offering access to diverse scaffolds and playing key roles in transformations such as aziridination, cyclopropanation, epoxidation, and nucleophilic processes. − At the same time, iodonium ylides have emerged as valuable reagents with rich reactivity in metal-mediated reactions, including arylation, cycloadditions, and cyclopropanation. − Despite these advances, approaches that exploit iodonium ylides for the preparation of S,C-sulfonium ylides remain poorly developed.

Moreover, extensive studies have focused on the reactions of N-acyl sulfenamides with various reagents, including alkyl halides, − aryl iodides, − arylboronic acids, , diazo compounds, − aryldiazonium salts, diaryliodonium salts, − alkenyl iodonium salts, aryl sulfonium salts, and other reagents − for the synthesis of sulfilimines in recent years (Figure b). However, the reaction between N-acyl sulfonamides and iodonium ylides for the synthesis of sulfilimines or S,C-sulfonium ylides has not yet been explored (Figure b). Despite the versatile reactivity of iodonium ylides, the potential of iodonium ylides in Doyle–Kirmse-type and transylidation reactions remains largely underdeveloped. The challenges include (a) identifying an efficient catalytic system to promote the divergent synthesis of homoallylic and allenic sulfides, selenides, and S,C-sulfonium ylides from iodonium ylides; (b) controlling the selective formation of S,C-sulfonium ylides and facilitating the subsequent [2,3]-sigmatropic rearrangement; and (c) expanding the substrate scope to accommodate structurally diverse iodonium ylides and sulfides.

In this study, we report a ruthenium-catalyzed Doyle–Kirmse-type reaction utilizing iodonium ylides, followed by a unique decarbonylation process, enabling the synthesis of novel homoallylic and allenic sulfur- and selenium-containing compounds (Figure c). By utilizing stable and nonexplosive iodonium ylides as carbene precursors, this approach mitigates the hazards associated with traditional diazo compounds, offering a safe and reliable strategy for carbon–sulfur, carbon–selenium, and carbon–carbon bond formation. Additionally, we also introduce a previously unreported ruthenium-catalyzed transylidation between N-acyl sulfenamides and iodonium ylides, providing efficient access to new S,C-sulfonium ylides under mild conditions (Figure c).

Results and Discussion

Optimization of Reaction Conditions for Doyle–Kirmse-Type and Decarbonylation Transformations

To optimize the reaction conditions, we initially selected 3-(phenyl-λ3-iodaneylidene)­chromane-2,4-dione (1a) and allyl­(phenyl)­sulfane (2a) as model substrates. First, various transition metal catalysts were evaluated including [RuCl2(p-cymene)]2, [Cp*RhCl2]2, Cp*Co­(CO)­I2, Rh2(OAc)4, and Pd­(OAc)2. Among these, [RuCl2(p-cymene)]2 afforded the highest yield of the desired homoallylic sulfide product (3a) via a Doyle–Kirmse-type reaction and a rare decarbonation process, while other catalysts gave inferior or negligible yields (Table , entries 1–5). Subsequent solvent screening indicated that dichloromethane, toluene, ethyl acetate, tetrahydrofuran, methanol, and hexafluoro-2-propanol (entries 6–11) failed to significantly enhance the reaction efficiency. In addition, the use of alternative additives such as NaOAc and Cs2CO3 (entries 12 and 13) resulted in decreased yields. Increasing the catalyst loading to 5 mol % (entry 14) led to only a marginal change in yield. Under stoichiometric optimization conditions (entry 15), the use of 0.14 mmol of 1a and 0.10 mmol of 2a afforded a 72% yield. Notably, increasing the amount of 1a to 0.20 mmol led to a significant improvement in the yield, reaching 81% (entry 16). These results demonstrated that the combination of [RuCl2(p-cymene)]2 and trifluoroethanol under air provided the most efficient conditions for this transformation.

1. Optimization of Reaction Conditions .

graphic file with name pc5c00098_0007.jpg

entry catalyst additive solvent yield (%)
1 [RuCl2(p-cymene)]2 - TFE 69
2 [Cp*RhCl2]2 - TFE 58
3 Cp*Co(CO)I2 - TFE 45
4 Rh2(OAc)4 - TFE 17
5 Pd(OAc)2 - TFE trace
6 [RuCl2(p-cymene)]2 - DCM 62
7 [RuCl2(p-cymene)]2 - toluene 51
8 [RuCl2(p-cymene)]2 - EA 48
9 [RuCl2(p-cymene)]2 - THF 48
10 [RuCl2(p-cymene)]2 - MeOH 21
11 [RuCl2(p-cymene)]2 - HFIP 63
12 [RuCl2(p-cymene)]2 NaOAc TFE 38
13 [RuCl2(p-cymene)]2 Cs2CO3 TFE 31
14 [RuCl2(p-cymene)]2 - TFE 70
15 [RuCl2(p-cymene)]2 - TFE 72
16 [RuCl2(p-cymene)]2 - TFE 81
Open in a new tab
a

Reaction conditions: 1a (0.1 mmol), 2a (0.12 mmol), [RuCl2(p-cymene)]2 (2.5 mol %), under air, TFE (2.0 mL), rt, and 12 h. Isolated yields are reported.

b

5 mol % [RuCl2(p-cymene)]2 was used.

c

0.14 mmol 1a and 0.1 mmol 2a were used.

d

0.2 mmol 1a and 0.1 mmol 2a were used.

Substrate Scope for Ru-Catalyzed Doyle–Kirmse-Type and Decarbonylation Transformations

Upon identifying optimal conditions, we proceeded to assess the breadth of the substrate scope (Scheme ). First, various coumarin-derived iodonium ylides 1 were reacted with allyl­(phenyl)­sulfane 2a. Substrates bearing halogen substituents (F, Cl, and Br), as well as methyl and methoxy groups at different positions on the coumarin ring, along with a naphthyl-substituted variant, furnished the corresponding products in good yields (3b–3k). Next, a systematic investigation of allyl sulfide 2 with 1a revealed notable substituent effects. The transformation displayed good functional group tolerance, accommodating both electron-donating groups (methoxy, methyl, isopropyl) and electron-withdrawing groups (bromo, fluoro, chloro) at various positions on the phenyl ring to deliver products 3l–3s in yields ranging from 47 to 75%. The strongly electron-withdrawing nitro group was also well tolerated, affording product 3t in 54% yield. When the phenyl group was replaced with a benzyl or methyl group, the desired products (3w and 3za) were obtained in good yields. In contrast, substitution with naphthyl, pyridyl, cyclohexyl, allyl, or propyl groups led to lower yields of the corresponding homoallylic sulfides (3u, 3v, 3x–3z). Additionally, a nonterminal alkene was also tolerated under the reaction conditions, affording 3zb in good yield.

1. Substrate Scope of Coumarin-Derived Iodonium Ylides and Allyl Sulfides .

1

Open in a new tab

a Reaction conditions: 1 (0.4 mmol), 2 (0.2 mmol), [RuCl2(p-cymene)]2 (2.5 mol %), under air, TFE (3.0 mL), rt, and 12 h. Isolated yields are reported.

In addition, when 1,3-dicarbonyl-derived iodonium ylides 4 were used in place of coumarin-derived iodonium ylides, the substrates successfully underwent a Doyle–Kirmse-type reaction to afford the corresponding homoallylic sulfides 5 (Scheme ). In general, a variety of allyl sulfides 2 exhibited good functional group tolerance, furnishing the desired products (5a–5l) in moderate to excellent yields. Functional groups such as tert-butyl, ester, and nitro (5b–5d) groups on the benzene ring, naphthyl, pyridyl, thienyl, benzyl, cyclohexyl, allyl, and methyl groups (5e–5k) were well tolerated. Furthermore, the methodology was compatible with a broad range of heterocyclic frameworks, including 4-hydroxy-1-methylquinolinone, pyridine-2,4­(1H,3H)-dione, and various cyclohexane-1,3-dione and cyclopentane-1,3-dione derivatives (5m–5s). Notably, noncyclic iodonium ylides were also effective under the reaction conditions, delivering products 5t and 5u in good yields. Additionally, the transformation showed good reactivity with allyl­(phenyl)­selane, affording product 5v in 65% yield. The noncyclic iodonium ylide reacted with phenyl­(prop-2-yn-1-yl)­sulfane, providing the corresponding allenyl sulfide 5w in 54% yield.

2. Substrate Scope of 1,3-Dicarbonyl-Derived Iodonium Ylides, Allyl Sulfides, Allyl Selenides, and Alkynyl Sulfides .

2

Open in a new tab

a Reaction conditions: 4 (0.2 mmol), 2 (0.28 mmol), [RuCl2(p-cymene)]2 (2.5 mol %), under air, TFE (3.0 mL), rt, and 12 h. Isolated yields are reported. b 0.1 mmol 4 and 0.14 mmol 2 were used.

Optimization of Reaction Conditions for the Synthesis of S,C-Sulfonium Ylides

Furthermore, the reaction between N-pivaloyl sulfenamide 6a and iodonium ylide 1a for the synthesis of S,C-sulfonium ylide 7a was also explored (see Supporting Information, Table S1). Initial optimization revealed that elevating the reaction temperature to 50 °C markedly improved the yield from 30 to 78% (Table S1, entries 1 and 2). Subsequently, a range of solvents, including DCE, EA, dioxane, and toluene, were evaluated (Table S1, entries 3–6). Among them, toluene proved to be the most effective, affording the highest yield of 88%, while the others resulted in significantly lower yields. Furthermore, replacing [RuCl2(p-cymene)]2 with alternative catalysts such as Cp*Co­(CO)­I2, [Cp*RhCl2]2, Rh2(esp)2, Pd­(OAc)2, or Rh2(OAc)2 led to no reaction (Table S1, entries 7–11).

With optimal conditions in hand, the substrate scope of N-acyl sulfenamides and iodonium ylides was explored (Scheme ). Initially, a variety of heterocycle-derived iodonium ylides, such as coumarin, 4-hydroxynaphthalene-1,2-dione, 4-hydroxy-1-methylquinolinone, 4-hydroxy-2H-pyrido­[1,2-a]­pyrimidin-2-one, 4-hydroxy-pyran-2-one, and pyridine-2,4­(1H,3H)-dione, were explored. The corresponding products (7a–7f) were obtained in good yields, demonstrating good compatibility with a broad range of heterocyclic scaffolds. Additionally, the incorporation of saturated heterocyclic systems (7g–7k) yielded products in 27–98% yields. Notably, noncyclic iodonium ylide was also tolerated, affording S,C-sulfonium ylides 7l smoothly. Next, various substituents on N-pivaloyl sulfenamides were explored. Both electron-donating and -withdrawing substituents on the phenyl ring were well tolerated (7m–7o, 73–94% yield). Moreover, the transformation remained effective when the phenyl group was replaced with a thiophene moiety, affording product 7p. Substitution of the pivaloyl group with an acetyl or benzoyl group also proceeded efficiently, delivering products in good yields (7q and 7r, 78–99%). Overall, these results collectively demonstrate that the ruthenium-catalyzed synthesis of S,C-sulfonium ylides exhibits a broad substrate scope and outstanding functional group tolerance.

3. Substrate Scope of N-Acyl Sulfenamides and Iodonium Ylides .

3

Open in a new tab

a Reaction conditions: 1/4 (0.2 mmol), 6 (0.3 mmol), [RuCl2(p-cymene)]2 (3 mol %), under air, toluene (3.0 mL), 50 °C, and 12 h. Isolated yields are reported.

Subsequently, a scale-up synthesis was conducted using 3-(phenyl-λ3-iodaneylidene)­chromane-2,4-dione (1a, 4.0 mmol) and allyl­(phenyl)­sulfane (2a, 2.0 mmol) under standard conditions, yielding product 3a in 66% yield (Figure a). Compound 3a was treated with acetic anhydride and DMAP in DCM at room temperature provided the ester 8a in 97% yield. In addition, 3a was reacted with iodocyclopentane in the presence of Cs2CO3 in DMF, affording product 8b in 43% yield. Furthermore, tunable oxidation with m-CPBA (3 or 5 equiv) selectively afforded compounds 8c and 8d, respectively. These results highlight the functional group transformation potential of compound 3, enabling the synthesis of structurally complex molecules bearing diverse functionalities.

2.

2

Open in a new tab

Scale-up synthesis and transformation experiments: (a) scale-up synthesis and (b) transformation experiments.

In addition, the reaction was carried out with the inclusion of radical scavengers, such as TEMPO or BHT, and the desired product 5a was still obtained in good yields. This observation suggests that a radical-mediated process is unlikely (Figure a). Based on preliminary mechanistic studies and relevant literature, ,, a plausible catalytic cycle is proposed (Figure b). In this mechanism, iodonium ylide 1/4 undergoes decomposition by the ruthenium catalyst to form ruthenium–carbene intermediate A. This intermediate subsequently reacts with allyl sulfide 2 or amide sulfides 6 to generate metal-associated zwitterionic intermediate B. This intermediate subsequently converts into sulfonium ylide 7, while simultaneously regenerating the active catalyst. When R is an allyl group, a [2,3]-sigmatropic rearrangement occurs, leading to the formation of compound 5. When X = O, this rearrangement is followed by a unique decarbonylation process, ultimately yielding homoallylic sulfide 3.

3.

3

Open in a new tab

Mechanistic studies: (a) free radical trapping experiments and (b) proposed catalytic cycle.

Conclusion

In summary, we disclose an unprecedented ruthenium-catalyzed Doyle–Kirmse-type transformation employing iodonium ylides. This strategy proceeds via a rare decarbonylation pathway to deliver structurally novel homoallylic and allenic sulfides and selenides. Moreover, this work also establishes a ruthenium-catalyzed transylidation process that couples N-acyl sulfenamides with cyclic iodonium ylides, affording diverse S,C-sulfonium ylides. These methods showcase broad applicability to various substrates, good tolerance for functional groups, mild reaction conditions, and scalability while employing an inexpensive, commercially available ruthenium catalyst. Scale-up experiments and downstream derivatizations underscore the synthetic utility of this method. Importantly, this work extends the Doyle–Kirmse reaction beyond classical diazo compounds, offering a practical and safe alternative for carbon–sulfur, carbon–selenium, and carbon–carbon bond formation, while simultaneously providing a valuable route for the synthesis of diverse sulfonium ylides, with potential applications in organic synthesis. By leveraging the unique reactivities of iodonium ylides, these transformations not only broaden the application scope of hypervalent iodine reagents but also harness ruthenium catalysis and coumarin-derived iodonium ylides to enable both rearrangement and decarbonylation.

Supplementary Material

pc5c00098_si_001.pdf (11.4MB, pdf)
pc5c00098_si_002.cif (226.2KB, cif)
pc5c00098_si_003.cif (278.8KB, cif)
pc5c00098_si_004.cif (637.5KB, cif)

Acknowledgments

Financial support from the National Natural Science Foundation of China (82404416) and the Zhongshan Science and Technology Bureau (CXTD2023009) is gratefully acknowledged.

The data underlying this study are available in the published article and its Supporting Information.

The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/prechem.5c00098.

  • General reaction procedures, characterization data of products, and NMR spectra of all products (PDF)

  • X-ray crystallographic data for 3j (CIF)

  • X-ray crystallographic data for 5a (CIF)

  • X-ray crystallographic data for 7o (CIF)

#.

Z.H. and L.W. contributed equally to this work.

The authors declare no competing financial interest.

References

  1. Ford A., Miel H., Ring A., Slattery C. N., Maguire A. R., McKervey M. A.. Modern Organic Synthesis with α-Diazocarbonyl Compounds. Chem. Rev. 2015;115:9981–10080. doi: 10.1021/acs.chemrev.5b00121. [DOI] [PubMed] [Google Scholar]
  2. Jia M., Ma S.. New Approaches to the Synthesis of Metal Carbenes. Angew. Chem., Int. Ed. 2016;55:9134–9166. doi: 10.1002/anie.201508119. [DOI] [PubMed] [Google Scholar]
  3. Bauer I., Knölker H. J.. Iron catalysis in organic synthesis. Chem. Rev. 2015;115:3170–3387. doi: 10.1021/cr500425u. [DOI] [PubMed] [Google Scholar]
  4. Shang R., Ilies L., Nakamura E.. Iron-Catalyzed C-H Bond Activation. Chem. Rev. 2017;117:9086–9139. doi: 10.1021/acs.chemrev.6b00772. [DOI] [PubMed] [Google Scholar]
  5. Xia Y., Qiu D., Wang J.. Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion. Chem. Rev. 2017;117:13810–13889. doi: 10.1021/acs.chemrev.7b00382. [DOI] [PubMed] [Google Scholar]
  6. Xia Y., Wang J.. N-Tosylhydrazones: versatile synthons in the construction of cyclic compounds. Chem. Soc. Rev. 2017;46:2306–2362. doi: 10.1039/C6CS00737F. [DOI] [PubMed] [Google Scholar]
  7. Zhu D., Chen L., Fan H., Yao Q., Zhu S.. Recent progress on donor and donor-donor carbenes. Chem. Soc. Rev. 2020;49:908–950. doi: 10.1039/C9CS00542K. [DOI] [PubMed] [Google Scholar]
  8. Empel C., Pham Q. H., Koenigs R. M.. Spin States Matter-from Fundamentals toward Synthetic Methodology Development and Drug Discovery. Acc. Chem. Res. 2024;57:2717–2727. doi: 10.1021/acs.accounts.4c00405. [DOI] [PubMed] [Google Scholar]
  9. Liu Z., Zhang X., Sivaguru P., Bi X.. Triftosylhydrazone in Single-Atom Skeletal Editing. Acc. Chem. Res. 2025;58:130–149. doi: 10.1021/acs.accounts.4c00709. [DOI] [PubMed] [Google Scholar]
  10. Kirmse W., Kapps M.. Reaktionen des Diazomethans mit Diallylsulfid und Allyläthern unter Kupfersalz-Katalyse. Chem. Ber. 1968;101:994–1003. doi: 10.1002/cber.19681010333. [DOI] [Google Scholar]
  11. Doyle M. P., Tamblyn W. H., Bagheri V.. Highly effective catalytic methods for ylide generation from diazo compounds Mechanism of the rhodium-and copper-catalyzed reactions with allylic compounds. J. Org. Chem. 1981;46:5094–5102. doi: 10.1021/jo00338a008. [DOI] [Google Scholar]
  12. Nishibayashi Y., Ohe K., Uemura S. J.. The first example of enantioselective carbenoid addition to organochalcogen atoms: application to [2, 3] sigmatropic rearrangement of allylic chalcogen ylides. J. Chem. Soc. Chem. Commun. 1995:1245–1246. doi: 10.1039/c39950001245. [DOI] [Google Scholar]
  13. Doyle M. P., Forbes D. C.. Recent Advances in Asymmetric Catalytic Metal Carbene Transformations. Chem. Rev. 1998;98:911–936. doi: 10.1021/cr940066a. [DOI] [PubMed] [Google Scholar]
  14. Zhang Y., Wang J.. Catalytic [2,3]-sigmatropic rearrangement of sulfur ylide derived from metal carbene. Coord. Chem. Rev. 2010;254:941–953. doi: 10.1016/j.ccr.2009.12.005. [DOI] [Google Scholar]
  15. West T. H., Spoehrle S. S. M., Kasten K., Taylor J. E., Smith A. D.. Catalytic Stereoselective [2,3]-Rearrangement Reactions. ACS Catal. 2015;5:7446–7479. doi: 10.1021/acscatal.5b02070. [DOI] [Google Scholar]
  16. Liao M., Wang J.. Highly efficient [2,3]-sigmatropic rearrangement of sulfur ylide derived from Rh­(ii) carbene and sulfides in water. Green. Chem. 2007;9:184–188. doi: 10.1039/B612743F. [DOI] [Google Scholar]
  17. McMillen D. W., Varga N., Reed B. A., King C.. Asymmetric copper-catalyzed. J. Org. Chem. 2000;65:2532–2536. doi: 10.1021/jo991842n. [DOI] [PubMed] [Google Scholar]
  18. Ma M., Peng L. L., Li C. K., Zhang X., Wang J. B.. Highly stereoselective [2, 3]-sigmatropic rearrangement of sulfur ylide generated through Cu (I) carbene and sulfides. J. Am. Chem. Soc. 2005;127:15016–15017. doi: 10.1021/ja055021d. [DOI] [PubMed] [Google Scholar]
  19. Zhou C. Y., Yu W. Y., Chan P. W., Che C. M.. Ruthenium porphyrin catalyzed tandem sulfonium/ammonium ylide formation and [2,3]-sigmatropic rearrangement. A concise synthesis of (±)-platynecine. J. Org. Chem. 2004;69:7072–7082. doi: 10.1021/jo049540v. [DOI] [PubMed] [Google Scholar]
  20. Li Z., Parr B. T., Davies H. M. L.. Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols. J. Am. Chem. Soc. 2012;134:10942–10946. doi: 10.1021/ja303023n. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. Greenman K. L., Carter D. S., Vranken D. L.. Palladium-catalyzed insertion reactions of trimethylsilyldiazomethane. Tetrahedron. 2001;57:5219–5225. doi: 10.1016/S0040-4020(01)00363-5. [DOI] [Google Scholar]
  22. Fukuda T., Irie R., Katsuki T.. Catalytic and asymmetric [2, 3]-sigmatropic rearrangement: Co (III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement. Tetrahedron. 1999;55:649–664. doi: 10.1016/S0040-4020(98)01065-5. [DOI] [Google Scholar]
  23. Davies P. W., Albrecht S. J.. Alkynes as masked ylides: gold-catalysed intermolecular reactions of propargylic carboxylates with sulfides. Chem. Commun. 2008;2:238–240. doi: 10.1039/B714813E. [DOI] [PubMed] [Google Scholar]
  24. Davies P. W. S., Albrecht J. C., Assanelli G.. Silver-catalysed Doyle-Kirmse reaction of allyl and propargyl sulfides. Org. Biomol. Chem. 2009;7:1276–1279. doi: 10.1039/b822584b. [DOI] [PubMed] [Google Scholar]
  25. Holzwarth M. S., Alt I., Plietker B.. Catalytic activation of diazo compounds using electron-rich, defined iron complexes for carbene-transfer reactions. Angew. Chem., Int. Ed. 2012;51:5351–5354. doi: 10.1002/anie.201201409. [DOI] [PubMed] [Google Scholar]
  26. Chen Y. T., Lv G. H., Li Z. Y., Ye M. L., Huang T. L., Hai L., Wu Y.. Rh­(II) catalyzed efficient sigmatropic rearrangement reaction of pyridotriazoles and sulfides. Green Synth. Catal. 2024;5:77–79. doi: 10.1016/j.gresc.2023.04.004. [DOI] [Google Scholar]
  27. Xu X. F., Li C., Tao Z. H., Pan Y. J.. Aqueous hemin catalyzed sulfonium ylide formation and subsequent [2,3]-sigmatropic rearrangements. Green Chem. 2017;19:1245–1249. doi: 10.1039/C6GC02681H. [DOI] [PubMed] [Google Scholar]
  28. Tyagi V., Sreenilayam G., Bajaj P., Tinoco A., Fasan R.. Biocatalytic Synthesis of Allylic and Allenyl Sulfides through a Myoglobin-Catalyzed Doyle-Kirmse Reaction. Angew. Chem., Int. Ed. 2016;55:13562–13566. doi: 10.1002/anie.201607278. [DOI] [PMC free article] [PubMed] [Google Scholar]
  29. Zhang Z., Sheng Z., Yu W., Wu G., Zhang R., Chu W. D., Zhang Y., Wang J.. Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides. Nat. Chem. 2017;9:970–976. doi: 10.1038/nchem.2789. [DOI] [PubMed] [Google Scholar]
  30. Wang B., Howard I. G., Pope J. W., Conte E. D., Deng Y.. Bis­(imino)­pyridine iron complexes for catalytic carbene transfer reactions. Chem. Sci. 2019;10:7958–7963. doi: 10.1039/C9SC02189B. [DOI] [PMC free article] [PubMed] [Google Scholar]
  31. He F., Jana S., Koenigs R. M.. Gold-Catalyzed Sigmatropic Rearrangement Reactions via Carbene Transfer Reactions. J. Org. Chem. 2020;85:11882–11891. doi: 10.1021/acs.joc.0c01678. [DOI] [PubMed] [Google Scholar]
  32. Lin X., Tang Y., Yang W., Tan F., Lin L., Liu X., Feng X.. Chiral Nickel­(II) Complex Catalyzed Enantioselective Doyle-Kirmse Reaction of α-Diazo Pyrazoleamides. J. Am. Chem. Soc. 2018;140:3299–3305. doi: 10.1021/jacs.7b12486. [DOI] [PubMed] [Google Scholar]
  33. Yang F. Y., Han T. J., Jia S. K., Wang M. C., Mei G. J.. Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle-Kirmse reaction. Chem. Commun. 2023;59:3107–3110. doi: 10.1039/D3CC00160A. [DOI] [PubMed] [Google Scholar]
  34. Midya S., Hari D. P.. A highly diastereoselective strain-release Doyle-Kirmse reaction: access to functionalized difluoro­(methylene)­cyclopropanes. Chem. Sci. 2023;14:13560–13567. doi: 10.1039/D3SC04749K. [DOI] [PMC free article] [PubMed] [Google Scholar]
  35. Zhang X., Liu Z., Yang X., Dong Y., Virelli M., Zanoni G., Anderson E. A., Bi X.. Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications. Nat. Commun. 2019;10:284. doi: 10.1038/s41467-018-08253-z. [DOI] [PMC free article] [PubMed] [Google Scholar]
  36. Ning Y., Zhang X., Gai Y., Dong Y., Sivaguru P., Wang Y., Reddy B. R. P., Zanoni G., Bi X.. Difluoroacetaldehyde N-Triftosylhydrazone (DFHZ-Tfs) as a Bench-Stable Crystalline Diazo Surrogate for Diazoacetaldehyde and Difluorodiazoethane. Angew. Chem., Int. Ed. 2020;59:6473–6481. doi: 10.1002/anie.202000119. [DOI] [PubMed] [Google Scholar]
  37. Zhang Y., Li S., Chen H., Song W., Ning Y., Liu Z., Wu Y., Murali K., Sivaguru P., Zhang X.. Dimethoxyacetaldehyde N-triftosylhydrazone: Preparation and Carbene Reactivity in Cyclopropanation and Doyle-Kirmse Reactions. Org. Lett. 2025;27:1941–1948. doi: 10.1021/acs.orglett.5c00223. [DOI] [PubMed] [Google Scholar]
  38. Jones A. C., May J. A., Sarpong R., Stoltz B. M.. Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements. Angew. Chem., Int. Ed. 2014;53:2556–2591. doi: 10.1002/anie.201302572. [DOI] [PMC free article] [PubMed] [Google Scholar]
  39. Scott K. A., Njardarson J. T.. Analysis of US FDA-approved drugs containing sulfur atoms. Top. Curr. Chem. 2018;376:5. doi: 10.1007/s41061-018-0184-5. [DOI] [PubMed] [Google Scholar]
  40. McGarrigle E. M., Myers E. L., Illa O., Shaw M. A., Riches S. L., Aggarwal V. K.. Chalcogenides as organocatalysts. Chem. Rev. 2007;107:5841–5883. doi: 10.1021/cr068402y. [DOI] [PubMed] [Google Scholar]
  41. Sun X. L., Tang Y.. Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes. Acc. Chem. Res. 2008;41:937–948. doi: 10.1021/ar800108z. [DOI] [PubMed] [Google Scholar]
  42. Jenks W. S., Heying M. J., Stoffregen S. A., Rockafellow E. M.. Reaction of dicarbomethoxycarbene with thiophene derivatives. J. Org. Chem. 2009;74:2765–2770. doi: 10.1021/jo802823s. [DOI] [PubMed] [Google Scholar]
  43. Jenks W. S., Heying M. J., Rockafellow E. M.. Modulation of carbene spin state population through precursor photophysics. Org. Lett. 2009;11:955–958. doi: 10.1021/ol802934w. [DOI] [PubMed] [Google Scholar]
  44. Ohno H.. Synthesis and applications of vinylaziridines and ethynylaziridines. Chem. Rev. 2014;114:7784–7814. doi: 10.1021/cr400543u. [DOI] [PubMed] [Google Scholar]
  45. Miura T., Fujimoto Y., Funakoshi Y., Murakami M.. A Reaction of Triazoles with Thioesters to Produce b-Sulfanyl Enamides by Insertion of an Enamine Moiety into the Sulfur–Carbonyl Bond. Angew. Chem., Int. Ed. 2015;54:9967–9970. doi: 10.1002/anie.201504013. [DOI] [PubMed] [Google Scholar]
  46. Liu X. S., Tang Z., Li Z., Li M., Xu L., Liu L.. Modular and Stereoselective Synthesis of Tetrasubstituted Vinyl Sulfides Leading to a Library of AIEgens. Nat. Commun. 2021;12:7298. doi: 10.1038/s41467-021-27167-x. [DOI] [PMC free article] [PubMed] [Google Scholar]
  47. Liu H. T., Chen F., Zhao N. N., Vummaleti S. V. C., Sullivan M. B., Ying J. Y., Wang L.. Rhodium-Catalyzed Ring Expansion Reactions for the Concise Construction of Densely Functionalized Oxathionines and Oxathiocines. ACS Catal. 2022;12:7524–7530. doi: 10.1021/acscatal.2c01529. [DOI] [Google Scholar]
  48. Pan S., Sk M. S., Sanyal B., Roy L., Samanta R.. Ru­(II)-Catalyzed [1,4]-Sigmatropic Rearrangement and Intramolecular Concerted SNAr of Aryl and Heteroarylthio Derivatives using Quinoid Carbene. ACS Catal. 2024;14:18419–18428. doi: 10.1021/acscatal.4c05272. [DOI] [Google Scholar]
  49. Ando W., Yagihara T., Tozune S., Imai I., Suzuki J., Toyama T., Nakaido S., Migita T.. Reactions of dimethyl diazomalonate with divalent sulfides. J. Org. Chem. 1972;37:1721–1727. doi: 10.1021/jo00976a010. [DOI] [Google Scholar]
  50. Gillespie R. J., Murray-Rust J., Murray-Rust P., Porter A. E. A.. Rhodium­(II)-catalysed addition of dimethyl diazomalonate to thiophen: a simple synthesis of thiophenium bismethoxycarbonylmethylides and crystal and molecular structure of the unsubstituted methylide. J. Chem. Soc., Chem. Commun. 1978:83–84. doi: 10.1039/c39780000083. [DOI] [Google Scholar]
  51. Stoffregen S. A., Heying M., Jenks W. S.. S,C-sulfonium ylides from thiophenes: potential carbene precursors. J. Am. Chem. Soc. 2007;129:15746–15747. doi: 10.1021/ja076351w. [DOI] [PubMed] [Google Scholar]
  52. Wang X. J., Liu H. H., Cheng J. K., Xiang S. H., Tan B.. Catalytic enantioselective synthesis of chiral sulfonium ylides with S-stereogenic center. Chem. 2023;9:1495–1504. doi: 10.1016/j.chempr.2023.02.017. [DOI] [Google Scholar]
  53. Bao W., Wang X. J., Wang S. H., Chen S. W., Liu H. H., Xiang S. H., Tan B.. Design of Stable Chiral Aminosulfonium Ylides and Their Catalytic Asymmetric Synthesis. Angew. Chem., Int. Ed. 2024;63:e202412508. doi: 10.1002/anie.202412508. [DOI] [PubMed] [Google Scholar]
  54. Müller P.. Asymmetric transfer of carbenes with phenyliodonium ylides. Acc. Chem. Res. 2004;37:243–251. doi: 10.1021/ar0202619. [DOI] [PubMed] [Google Scholar]
  55. Spyroudis S., Malamidou-Xenikaki E.. Zwitterionic Iodonium Compounds: Useful Tools in Organic Synthesis. Synlett. 2008;18:2725–2740. doi: 10.1055/s-2008-1078261. [DOI] [Google Scholar]
  56. Yusubov M. S., Akira Y., Viktor V.. Iodonium ylides in organic synthesis. Arkivoc. 2017;2016:342–374. doi: 10.3998/ark.5550190.p009.732. [DOI] [Google Scholar]
  57. Chelli S., Troshin K., Mayer P., Lakhdar S., Ofial A. R., Mayr H.. Nucleophilicity Parameters of Stabilized Iodonium Ylides for Characterizing Their Synthetic Potential. J. Am. Chem. Soc. 2016;138:10304–10313. doi: 10.1021/jacs.6b05768. [DOI] [PubMed] [Google Scholar]
  58. Moriarty R. M., Prakash O., Vaid R. K., Zhao L.. A novel intramolecular cyclopropanation using iodonium ylides. J. Am. Chem. Soc. 1989;111:6443–6444. doi: 10.1021/ja00198a078. [DOI] [Google Scholar]
  59. Chidley T., Jameel I., Rizwan S., Peixoto P. A., Pouységu L., Quideau S., Hopkins W. S., Murphy G. K.. Blue LED Irradiation of Iodonium Ylides Gives Diradical Intermediates for Efficient Metal-free Cyclopropanation with Alkenes. Angew. Chem., Int. Ed. 2019;58:16959–16965. doi: 10.1002/anie.201908994. [DOI] [PubMed] [Google Scholar]
  60. Epping R. F. J., Hoeksma M. M., Bobylev E. O., Mathew S., De Bruin B.. Cobalt­(II)-tetraphenylporphyrin-catalysed carbene transfer from acceptor-acceptor iodonium ylides via N-enolate-carbene radicals. Nat. Chem. 2022;14:550–557. doi: 10.1038/s41557-022-00905-4. [DOI] [PubMed] [Google Scholar]
  61. Zhu Q., Wu J., Fathi R., Yang Z.. Phenyliodonium zwitterion as an efficient electrophile in the palladium-catalyzed suzuki-type reaction: a novel method for the synthesis of 3-aryl-4-hydroxycoumarins. Org. Lett. 2002;4:3333–3336. doi: 10.1021/ol020159b. [DOI] [PubMed] [Google Scholar]
  62. Liang M., He M., Zhong Z., Wan B., Du Q., Mai S.. Catalytic and Base-free Suzuki-type α-Arylation of Cyclic 1,3-Dicarbonyls via a Cyclic Iodonium Ylide Strategy. Angew. Chem., Int. Ed. 2024;63:e202400741. doi: 10.1002/anie.202400741. [DOI] [PubMed] [Google Scholar]
  63. Nunewar S., Kumar S., Talakola S., Nanduri S., Kanchupalli V.. Co­(III), Rh­(III) & Ir­(III)-Catalyzed Direct C-H Alkylation/Alkenylation/Arylation with Carbene Precursors. Chem. Asian J. 2021;16:443–459. doi: 10.1002/asia.202001219. [DOI] [PubMed] [Google Scholar]
  64. Kumar S., Borkar V., Mujahid M., Nunewar S., Kanchupalli V.. Iodonium ylides: an emerging and alternative carbene precursor for C-H functionalizations. Org. Biomol. Chem. 2022;21:24–38. doi: 10.1039/D2OB01644C. [DOI] [PubMed] [Google Scholar]
  65. Liao J., Kong D., Gao X., Zhai R., Chen X., Wang S.. Transition-Metal-Catalyzed Directed C-H Bond Functionalization with Iodonium Ylides: A Review of the Last 5 Years. Molecules. 2024;29:3567. doi: 10.3390/molecules29153567. [DOI] [PMC free article] [PubMed] [Google Scholar]
  66. Yoshimura A., Zhdankin V. V.. Recent Progress in Synthetic Applications of Hypervalent Iodine­(III) Reagents. Chem. Rev. 2024;124:11108–11186. doi: 10.1021/acs.chemrev.4c00303. [DOI] [PMC free article] [PubMed] [Google Scholar]
  67. Jiang Y., Li P., Zhao J., Liu B., Li X.. Iodonium Ylides as Carbene Precursors in Rh­(III)-Catalyzed C-H Activation. Org. Lett. 2020;22:7475–7479. doi: 10.1021/acs.orglett.0c02618. [DOI] [PubMed] [Google Scholar]
  68. Liu X. Q., Shi S. J., Ding W. Q., He Z. Y., Shen Y.. et al. Accessing 7,8-Dihydroquinoline-2,5-diones via Rh-Catalyzed Olefinic C-H Activation/[4 + 2] Cyclization. Org. Lett. 2024;26:5136–5140. doi: 10.1021/acs.orglett.4c01536. [DOI] [PubMed] [Google Scholar]
  69. Zhu C., Yoshimura A., Ji L., Wei Y., Nemykin V. N., Zhdankin V. V.. Design, preparation, X-ray crystal structure, and reactivity of O-alkoxyphenyliodonium bis­(methoxycarbonyl)­methanide, a highly soluble carbene precursor. Org. Lett. 2012;14:3170–3173. doi: 10.1021/ol301268j. [DOI] [PubMed] [Google Scholar]
  70. Chen Y., Fang D. M., Huang H. S., Nie X. K., Zhang S. Q., Cui X., Tang Z., Li G. X.. Synthesis of Sulfilimines via Selective S-C Bond Formation in Water. Org. Lett. 2023;25:2134–2138. doi: 10.1021/acs.orglett.3c00604. [DOI] [PubMed] [Google Scholar]
  71. Champlin A. T., Ellman J. A.. Preparation of Sulfilimines by Sulfur-Alkylation of N-Acyl Sulfenamides with Alkyl Halides. J. Org. Chem. 2023;88:7607–7614. doi: 10.1021/acs.joc.3c00750. [DOI] [PMC free article] [PubMed] [Google Scholar]
  72. Huang G., Lu X., Yang K., Xu X.. Redox-Neutral Synthesis of Sulfilimines through the S-Alkylation of Sulfenamides. Org. Lett. 2023;25:3173–3178. doi: 10.1021/acs.orglett.3c01060. [DOI] [PubMed] [Google Scholar]
  73. Wang F., Xiang W., Xie Y., Huai L., Zhang L., Zhang X.. Synthesis of chiral sulfilimines by organocatalytic enantioselective sulfur alkylation of sulfenamides. Sci. Adv. 2024;10:eadq2768. doi: 10.1126/sciadv.adq2768. [DOI] [PMC free article] [PubMed] [Google Scholar]
  74. Greenwood N. S., Ellman J. A.. Sulfur-Arylation of Sulfenamides via Ullmann-Type Coupling with (Hetero)­aryl Iodides. Org. Lett. 2023;25:4759–4764. doi: 10.1021/acs.orglett.3c01874. [DOI] [PMC free article] [PubMed] [Google Scholar]
  75. He M., Zhang R., Wang T., Xue X. S., Ma D.. Assembly of (hetero)­aryl sulfilimines via copper-catalyzed enantioselective S-arylation of sulfenamides with (hetero)­aryl Iodides. Nat. Commun. 2025;16:2310. doi: 10.1038/s41467-025-57474-6. [DOI] [PMC free article] [PubMed] [Google Scholar]
  76. He M., Zhang R., Ma D.. Assembly of (Hetero)­aryl Sulfoximines via Copper-Catalyzed S-Arylation of Sulfinamides with (Hetero)­aryl Halides. Org. Lett. 2025;27:2947–2951. doi: 10.1021/acs.orglett.5c00535. [DOI] [PubMed] [Google Scholar]
  77. Liang Q., Wells L. A., Han K., Chen S., Kozlowski M. C., Jia T.. Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides. J. Am. Chem. Soc. 2023;145:6310–6318. doi: 10.1021/jacs.2c12947. [DOI] [PMC free article] [PubMed] [Google Scholar]
  78. Greenwood N. S., Ellman J. A.. Sulfur-Arylation of Sulfenamides via Chan-Lam Coupling with Boronic Acids: Access to High Oxidation State Sulfur Pharmacophores. Org. Lett. 2023;25:2830–2834. doi: 10.1021/acs.orglett.3c00779. [DOI] [PMC free article] [PubMed] [Google Scholar]
  79. Greenwood N. S., Champlin A. T., Ellman J. A.. Catalytic Enantioselective Sulfur Alkylation of Sulfenamides for the Asymmetric Synthesis of Sulfoximines. J. Am. Chem. Soc. 2022;144:17808–17814. doi: 10.1021/jacs.2c09158. [DOI] [PMC free article] [PubMed] [Google Scholar]
  80. Patel S., Greenwood N. S., Mercado B. Q., Ellman J. A.. Rh­(II)-Catalyzed Enantioselective S-Alkylation of Sulfenamides with Acceptor-Acceptor Diazo Compounds Enables the Synthesis of Sulfoximines Displaying Diverse Functionality. Org. Lett. 2024;26:6295–6300. doi: 10.1021/acs.orglett.4c02402. [DOI] [PMC free article] [PubMed] [Google Scholar]
  81. Wu X., Chen M., He J., Wu J.. Synthesis of functionalized sulfilimines via iron-catalyzed sulfur alkylation of sulfenamides with diazo compounds. Green Chem. 2023;25:9092–9096. doi: 10.1039/D3GC03528J. [DOI] [Google Scholar]
  82. Xiao Z., Pu M., Li Y., Yang W., Wang F., Feng X., Liu X.. Asymmetric Catalytic Synthesis of Allylic Sulfenamides from Vinyl α-Diazo Compounds by a Rearrangement Route. Angew. Chem., Int. Ed. 2025;64:e202414712. doi: 10.1002/anie.202414712. [DOI] [PubMed] [Google Scholar]
  83. Yuan Y., Han Y., Zhang Z. K., Sun S., Wu K., Yang J., Zhang J.. Enantioselective Arylation of Sulfenamides to Access Sulfilimines Enabled by Palladium Catalysis. Angew. Chem., Int. Ed. 2024;63:e202409541. doi: 10.1002/anie.202409541. [DOI] [PubMed] [Google Scholar]
  84. Zhou Q., Li J., Wang T., Yang X.. Base-Promoted S-Arylation of Sulfenamides for the Synthesis of Sulfilimines. Org. Lett. 2023;25:4335–4339. doi: 10.1021/acs.orglett.3c01436. [DOI] [PubMed] [Google Scholar]
  85. Wu X. B., Shen Y., Jiang H. J., Gong L. Z.. Cu-Catalyzed Enantioselective S-Arylation of Sulfenamides Enabled by Confined Ligands. Org. Lett. 2025;27:2845–2851. doi: 10.1021/acs.orglett.5c00132. [DOI] [PubMed] [Google Scholar]
  86. Wu X., Li Y., Chen M., He F. S., Wu J.. Metal-Free Chemoselective S-Arylation of Sulfenamides To Access Sulfilimines. J. Org. Chem. 2023;88:9352–9359. doi: 10.1021/acs.joc.3c00961. [DOI] [PubMed] [Google Scholar]
  87. Huang G., Lu X., Liang F.. Redox-Neutral Strategy for Sulfilimines Synthesis via S-Arylation of Sulfenamides. Org. Lett. 2023;25:3179–3183. doi: 10.1021/acs.orglett.3c01077. [DOI] [PubMed] [Google Scholar]
  88. Zhao X., Xu Y.. Copper-catalyzed S-vinylation of sulfenamides for the synthesis of α,β-unsaturated sulfilimines. Cell Rep. Phys. Sci. 2024;5:102304. doi: 10.1016/j.xcrp.2024.102304. [DOI] [Google Scholar]
  89. Zhang M. J., Tan Y. H., Yang H. H., Fu X. Y., Liu Y. X.. et al. Dual Copper/Photoredox Catalysis for Radical-Mediated Arylation and Alkylation of Sulfenamides. ACS Catal. 2025;15:4007–4016. doi: 10.1021/acscatal.5c00082. [DOI] [Google Scholar]
  90. Yang G. F., Huang H. S., Nie X. K., Zhang S. Q., Cui X., Tang Z., Li G. X.. One-Pot Tandem Oxidative Bromination and Amination of Sulfenamide for the Synthesis of Sulfinamidines. J. Org. Chem. 2023;88:4581–4591. doi: 10.1021/acs.joc.3c00042. [DOI] [PubMed] [Google Scholar]
  91. Huang G., Ye J., Bashir M. A., Chen Y., Chen W., Lu X.. Hypervalent Iodine Mediated Synthesis of Sulfinamidines from Sulfenamides. J. Org. Chem. 2023;88:11728–11734. doi: 10.1021/acs.joc.3c00999. [DOI] [PubMed] [Google Scholar]
  92. Li M., Wang J., Ou X., Yu J.. Bronsted acid-catalyzed synthesis of sulfinamidines and sulfinimidate esters through electrophilic fluorination and substitution. Org. Biomol. Chem. 2025;23:3171–3176. doi: 10.1039/D5OB00139K. [DOI] [PubMed] [Google Scholar]
  93. Lu X., Huang G., Ye J., Bashir M. A., Su J., Yang K., Liang F., Xu X.. Hypervalent Iodine-Mediated Synthesis of Sulfinimidate Esters from Sulfenamides. Org. Lett. 2023;25:2151–2156. doi: 10.1021/acs.orglett.3c00678. [DOI] [PubMed] [Google Scholar]
  94. Wu X., Chen M., He F. S., Wu J.. Synthesis of Sulfilimines via Aryne and Cyclohexyne Intermediates. Org. Lett. 2023;25:5157–5161. doi: 10.1021/acs.orglett.3c01918. [DOI] [PubMed] [Google Scholar]
  95. Guo Y., Zhuang Z., Feng X., Ma Q., Li N., Jin C., Yoshida H., Tan J.. Selective S-Arylation of Sulfenamides with Arynes: Access to Sulfilimines. Org. Lett. 2023;25:7192–7197. doi: 10.1021/acs.orglett.3c02785. [DOI] [PubMed] [Google Scholar]
  96. Fimm M., Saito F.. Enantioselective Synthesis of Sulfinamidines via Asymmetric Nitrogen Transfer from N-H Oxaziridines to Sulfenamides. Angew. Chem., Int. Ed. 2024;63:e202408380. doi: 10.1002/anie.202408380. [DOI] [PubMed] [Google Scholar]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

pc5c00098_si_001.pdf (11.4MB, pdf)
pc5c00098_si_002.cif (226.2KB, cif)
pc5c00098_si_003.cif (278.8KB, cif)
pc5c00098_si_004.cif (637.5KB, cif)

Data Availability Statement

The data underlying this study are available in the published article and its Supporting Information.

Articles from Precision Chemistry are provided here courtesy of American Chemical Society

RESOURCES