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. 2026 Mar 10;11(11):18419–18426. doi: 10.1021/acsomega.6c00595

Potassium tert-Butoxide-Mediated Isomerization of Alkenes: A Versatile Protocol for Miscellaneous Substrates

Héctor Mario Heras Martínez 1, Sydney M Hampton 1, Stephen R Isbel 1, Chase N MacFarlane 1, Enrique B Aparicio 1, Ever A Blé-González 1, Alejandro Bugarin 1,*
PMCID: PMC13019183  PMID: 41908469

Abstract

The development of rapid and efficient routes to alkene derivatives remains a significant priority due to their broad utility as building blocks and valuable compounds. Herein, we report a simple, general, and highly efficient procedure for the (catalytic) isomerization of alkenes under mild conditions. This method is applicable to a wide range of substrates, including allylic derivatives of benzenes, aromatic and aliphatic systems, heterocycles, ethers, thioethers, amines, and sulfones. In this transformation, KO t Bu acts as both the base and the proton shuttle, enabling the reaction to proceed under air and affording quantitative yields within minutes for the majority of the substrates examined. The reaction occurs under thermodynamic control, affording the most stable isomer (typically, the E-alkene).

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Introduction

Alkene isomerization is a fundamental transformation in organic chemistry that involves the migration, “chain-walking,” of double bonds within a molecule. , This seemingly simple transformation holds immense synthetic value, offering an atom-economical and straightforward approach to access diverse alkene isomers. The ability to precisely control both the position and the stereochemistry of the double bonds is crucial, as different alkene isomers exhibit distinct physical and chemical properties, making them pervasive intermediates across numerous chemical processes, particularly in the chemical industry, where alkenes are considered fine chemical feedstocks, flavor and fragrance components, building blocks, and valuable pharmaceutical intermediates. −

Alkene isomerization presents two major challenges: controlling regioselectivity and stereoselectivity. ,− In this context, the most direct and efficient strategy for accessing internal alkenes is the isomerization of terminal alkenes, an approach that has garnered sustained attention, as it enables quick access to regio- and stereochemically defined alkenes from simple precursors (Figure , top). Over the past few decades, a few methods have been developed to mediate alkene isomerization that, to our knowledge, represent the best methods currently available to isomerize a broad range of alkenes (Figure , middle). In 2022, Morrill reported a borane-catalyzed isomerization of a myriad of terminal alkenes, albeit using a high temperature (150 °C), long reaction times (up to 2 days), and an inert atmosphere (Ar). In the same year, Cook reported the use of Ni­(NHC) and silane to perform catalytic isomerization of alkenes under slightly milder conditions (70 °C, 7 h, N2), while Leyva-Pérez disclosed a Ru-catalyzed (ppm loading) isomerization of miscellaneous terminal alkenes to Z-isomers, at elevated temperatures (150–200 °C). In 2024, Stephenson described also a ruthenium-catalyzed isomerization to E-alkenes under notably mild conditions (MeCN, rt, and 3 h), which in our opinion is one of the best methods to accomplish this transformation. In the same year, Luo and Zeng reported a chromium-catalyzed chain walk, also for a broad substrate scope, but requiring excess magnesium (2 equiv), to selectively move the double bond by one or two positions. Most recently, Jia et al. reported an elegant electrochemical isomerization of assorted alkenes favoring the E -isomer.

1.

1

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General methods for alkene isomerizations.

Beyond what we consider the best documented isomerization strategies discussed above, alkene isomerizations have been achieved using a plethora of different methods. Traditionally, the most widely used and selective protocols rely on transition-metal catalysts such as Ru, ,− Ir, , Co, − Ni, ,, Fe, , Mo, and Pd. , While these methods provide good control over regio- and stereoselectivity, they depend on expensive or sensitive catalysts. Alternatively, base-mediated isomerization represents a simpler and more economical option. For instance, potassium tert-butoxide (KO t Bu) has been known to promote allyl ether isomerization since the 1960s, , and has been applied to isomerize allyl aryls in total synthesis. Other bases such as NaO t Bu, LDA, KOH, NaN­(SiMe3)2, crown ether-base pairs, organomagnesium clusters, and nonionic bases like proazaphosphatranes have also been employed. In some cases, these protocols tolerate air and avoid the use of transition-metal catalysts entirely, which is particularly advantageous for scale-up syntheses. As a result, alternative base-mediated methods have emerged as powerful and economical alternatives, typically operating under an ambient atmosphere and mild temperatures (25–60 °C). However, some efforts have shifted toward more sustainable methods, including electrochemical reactions, dual visible-light cobalt catalysis, and light-driven isomerization of internal to external alkenes. For example, Nicewicz and co-workers reported a visible-light-induced E/Z isomerization via single-electron oxidation of electron-rich alkenes, providing access to both stereoisomers under mild conditions. In addition, Huang recently disclosed a tandem electrochemical process that converts terminal alkenes into alcohols via isomerization to internal alkenes followed by coupling with ketones. Lastly, Hou reported a scandium-catalyzed, Z-selective alkene isomerization that complements existing methods favoring Z-alkene formation.

The wide range of synthetic methods that have appeared in the literature reflects the diverse applications that alkene isomerizations can have. For example, tandem alkene isomerizations have been used in coupling reactions, , [2 + 2] and [4 + 2] cycloadditions, rearrangements, silylations, arylations, alkylations, metathesis reactions, , synthesis of heterocycles, unusual amino acids, acetamides, chromenes, amines, and key intermediates in total synthesis, , among many others. Therefore, it is valid to say that isomerized alkenes are synthetically useful building blocks. However, despite the wealth of available methodologies, there remains a clear need for milder, transition-metal-free, and versatile methods capable of delivering well-defined internal alkenes across a broad substrate scope. To address this gap, we herein report an efficient alkene isomerization strategy that employs readily available starting materials (Figure , bottom) to furnish the desired adducts in excellent yields and short reaction times. Importantly, the reaction conditions can be easily tunable to enable access to additional compound classes, as described in the Results and Discussion, highlighting the complementary reactivity of this method for generating valuable scaffolds relevant to drug discovery and materials science, without the need for transition metals or protective atmospheres.

Results and Discussion

The optimization of our protocol was initiated from an observation made while studying a direct allylic halogenation of allylbenzene (1a) in the presence of potassium tert-butoxide (KO t Bu) in DMSO-d 6. It was observed that 1.1 equiv of KO t Bu promoted full conversion of 1a to a new adduct (initially difficult to identify due to deuterium incorporation). However, after a few more experiments, we were able to identify the adduct as 2a. To our delight, this alkene isomerization was completed really fast (minutes) and at room temperature (∼22 °C). To validate this, we first run the experiment in DMSO, where no reaction was observed in the absence of KO t Bu (Table , entry 1). However, the addition of KO t Bu (0.25 equiv) catalyzed the reaction affording the isomerization adduct 2a in quantitative yield after only 10 min (entry 2). Other quantities of KO t Bu either did not complete the reaction (<0.25 equiv) or form the product as expected (>0.5 equiv) (not shown). Both DMSO and DMF proved to be the best solvents (entries 2 and 16, >99%), followed by MeCN (23%, entry 17) and ethanol (3%, entry 18); other nonpolar or protic solvents were ineffective. The bases Et3N, i Pr2EtN, and pyridine alsopromoted the reaction, but gave yields lower than KO t Bu. DMAP (entry 14), DBU (entry 15), and carbonate bases (entries 6–10) were inefficient bases. High yields were observed with NaO t Bu and LiO t Bu (98% and 91%, respectively), while KOH afforded the adduct in 97% yield, albeit using 0.5 equiv (entry 5). Furthermore, the reaction proceeded in quantitative yield under both dark and inert atmosphere, indicating that neither light nor oxygen affects the reaction (entries 19 and 20). Therefore, KO t Bu was chosen as the base and DMSO as the solvent to investigate the substrate scope.

1. Optimization of Reaction Conditions .

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entry time (min) base (0.25 equiv) solvent yield (%)
1 120 none DMSO NR
2 10 KO t Bu DMSO >99
3 10 NaO t Bu DMSO 98
4 10 LiO t Bu DMSO 91
5 120 KOH DMSO 97
6 120 Li2CO3 DMSO NR
7 120 Na2CO3 DMSO NR
8 120 K2CO3 DMSO NR
9 120 Cs2CO3 DMSO NR
10 120 CaCO3 DMSO NR
11 120 Et3N DMSO 10
12 120 i-Pr2EtN DMSO 5
13 120 Pyridine DMSO traces
14 120 DMAP DMSO NR
15 120 DBU DMSO NR
16 10 KO t Bu DMF 99
17 120 KO t Bu MeCN 23
18 120 KO t Bu Ethanol 3
19 10 KO t Bu DMSO >99
20 10 KO t Bu DMSO >99
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a

Reactions were carried out with allylbenzene 1a (0.4 mmol, 53 μL, 1 equiv), base (0.1 mmol, 0.25 equiv), in 1.0 mL of DMSO at room temperature (∼22 °C). Then, the mixture was stirred for 10 min, analyzed by 1H NMR using DMS0-d 6 as the solvent, and mesitylene as the internal standard. Those unreacted after 10 min were analyzed again at 2 h.

b

Isolated yields using silica gel flash chromatography.

c

0.5 equiv of KOH was used.

d

Dark.

e

Argon atmosphere. NR = no reaction.

With the optimal conditions established, the substrate scope was assessed (Table ). Diverse allylbenzenes were well tolerated under the standard reaction conditions, affording the corresponding adducts in excellent yields with high E-stereoselectivity. The parent allylbenzene furnished its styrene adduct in 95% yield. Both electron-withdrawing (2c, CF3, 97%) and electron-donating substituents (2e, OMe, 93%) were tolerated. Para-substituted derivatives (2b, Me and 2d, F) were obtained in 94 and 90%, respectively. Ortho-substituted moieties provided the desired products (2f, OMe and 2g, Br) in 98 and 95%, respectively. Similarly, Meta-substituted allylbenzenes (2h, methyl eugenol and 2i, safrole) gave excellent yields of 98 and 95%, respectively. The most sterically hindered substrate, 2-allylmesitylene, afforded its respective product 2j in 93% yield but with a 2:1 E/Z ratio, presumably due to steric effects from the two ortho substituents. Finally, 1-allylnaphthalene proved to be an excellent substrate, affording 2k in 99% yield. It is worth noting that all allylic starting materials exhibited similar R f values to their respective styrene products; therefore, all of the reactions were run to full conversion (10 min) to ensure complete product formation. The slightly lower isolated yields reflect product loss during purification by silica gel flash chromatography; otherwise, the yields could have been reported as quantitative for all substrates.

2. Scope of Allylbenzene Derivatives .

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a

Reactions were carried out with allylbenzene derivative 1a–k (0.4 mmol, 1 equiv), KO t Bu (0.1 mmol, 0.25 equiv), in 1.0 mL of DMSO at room temperature (∼22 °C). Then, the mixture was stirred for 10 min in open air.

b

Isolated yields based on 1, using silica gel flash chromatography.

c

E/Z > 20/1 unless noted in parentheses.

After the successful production of miscellaneous trans-β-methylstyrene derivatives 2 (Table ), the scope of special allyl substrates was evaluated (Table ). First, (2-methylpropenyl)­benzene 1l was reacted under the standard reaction conditions and, to our delight, having an extra substitution on the alkene did not diminish the reactivity, affording adduct 2l in 92% yield. Then, 3-allylpyridine 1m was subjected to the same reaction conditions to produce its adduct 2m in 80% yield. Encouraged by this result, another heterocycle, 1N-allylimidazole 1n, was reacted and the adduct 2n was obtained in 91% yield and 6:1 E/Z ratio. Next, other allylic systems were investigated; first allylthiother 1o was studied affording 2o in 92% but in 1:1 E/Z ratio. Furthermore, allyl ether 1p was studied affording 2p in 97%, but this time only the Z stereoisomer was observed, matching prior reported studies. − To further confirm this difference in stereoselectivity, two adducts containing both the allylbenzene and the allyl ethers were reacted, and as expected, adducts 2q and 2r were obtained in very high yields (93% and 96%) and excellent stereoselectivity, E for the styrene and Z for the vinyl ethers moieties, again confirming the trend.

3. Scope of Special Allylic Derivatives .

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a

Reactions were carried out with allyl derivative 1l–r (0.4 mmol, 1 equiv), KO t Bu (0.1 mmol, 0.25 equiv), in 1.0 mL of DMSO at room temperature (∼22 °C). Then, the mixture was stirred for 10 min in open air.

b

Isolated yields based on 1, using silica gel flash chromatography.

c

E/Z > 20/1 unless noted in parentheses.

The scope of less or nonactivated alkenes was also evaluated (Table ). Under the standard reaction conditions, these substrates failed to undergo the isomerization. However, modification of the initial conditions proved to be effective. For example, 4-phenylbutene 1s was fully converted to trans-β-ethylstyrene 2s using 1 equiv of KO t Bu and stirred for 2 h at 50 °C. However, since 2s is a volatile compound, only 65% yield was isolated. With the modified conditions, 1-hexene produced a mixture of the expected adducts along with multiple inseparable byproducts. At 110 °C, limonene 1u furnished cymene in 10%; although the yield is low, this result demonstrates the versatility of our method, as it promotes not only isomerization but also aromatization in the presence of air. Then at 80 °C, 1,5-cyclooctadiene 1v was efficiently converted to conjugated 1,3-cycloactadiene 2v in 99% yield. Interestingly, vinyl cyclohexane 1w was unreactive under the modified conditions, whereas allyl cyclohexane 1x decomposed. Lastly, 4-methyl-1-pentene 1y also presented a mixture of adducts, consistent with those previously observed for 1-hexene.

4. Scope of Alkene Derivatives .

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a

Reactions were carried out with alkene 1s–y (0.4 mmol, 1 equiv), KO t Bu (0.8 mmol, 2.0 equiv), in 1.0 mL of DMSO at room temperature (50–110 °C). Then, the mixture was stirred for 2 h in open air.

b

Isolated yields based on 1, using silica gel flash chromatography.

c

100% conversion, but the volatility of 2s diminished the isolated yield to 65%. Dec = decomposed.

Allylphenols and alcohols were also investigated (Table ). Initially, 2-allyllphenol 1z was subjected to modified conditions, 2 equiv of KO t Bu and stirred for 10 min at 50 °C, where 1 equiv of KO t Bu was used to quench the acidic proton. To our satisfaction, adduct 2z was obtained in 85% yield, albeit with a 9:1 E/Z ratio. The acetylated version 1aa was also reacted and as expected, the acetyl group was removed to give 2z in 84% yield, with the same 9:1 E/Z ratio. Then, eugenol was subjected to the same reaction conditions furnishing its adduct 2ab in 83% yield and 2.5:1 E/Z ratio. Then, 1-phenylprop-2-en-1-ol 1ac was reacted to furnish ketone 2ac in 98% yield via isomerization followed by tautomerization. To accomplish both reactions, this substrate had to be stirred at 80 °C for 2 h employing 2 equiv of KO t Bu. Similarly, 1-phenylbut-3-en-1-ol 1ad furnishes ketone 2ad in 96% yield. Finally, distinct reactivity was observed for the special substrates. For instance, 4-nitro allylphenol 1ae was unreactive under the standard conditions (Table ). However, upon increasing the base loading to 2 equiv and stirring the reaction at 50 °C for 30 min, deallylation occurred producing 4-nitrophenol 2ae in 88% yield, consistent with literature precedents for deallylation of allylic nitrophenols. − A similar outcome was observed with N-allyl aniline 1af, which produced aniline 2af in quantitative yield, but some mass was lost during purification to give 57% isolated yield. Last but not least, allyl sulfones 1ag and 1ah were efficiently deallylated even under the standard reaction conditions (Table ), forming benzenesulfonic acid 2ag and tolylsulfonic acid 2ah, in 95% and 96% yield, respectively (Table ).

5. Scope of Allyl Phenols, Alcohols, and Derivatives .

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a

Reactions were carried out with alkene 1z–1ah (0.4 mmol, 1 equiv), KO t Bu (0.1–0.8 mmol, 0.25–2.0 equiv), in 1.0 mL of DMSO at ∼22–80 °C. Then, the mixture was stirred for 10–120 min in open air.

b

Isolated yields based on 1, using silica gel flash chromatography.

The mechanism of alkene isomerization depends on the nature of the substrate and reaction conditions, but in general, base-mediated isomerization of allylbenzenes proceeds through an E1cb-like mechanism. , This process involves deprotonation at the allylic position, followed by protonation at a different site, resulting in the migration of the double bond. Since our reaction conditions favor thermodynamic control, the more stable E-alkene was observed. An exception was observed for allyl phenyl ether 1p, where the Z-alkene was exclusively obtained, presumably due to the oxygen’s lone pair interaction with the developing carbanion and/or the potassium ion, which stabilizes the transition state conformation during the protonation step. This observation is consistent with the literature precedents. Notably, proton shuttle was observed when allylbenzene was reacted in DMSO-d6, with deuterium incorporation at different positions depending on base equivalents and temperature (not shown). ,, In contrast, the reaction of allyl phenyl ether in DMSO-d6 yielded exclusively the Z-isomer, with no detectable deuterium incorporation, further supporting a distinct mechanism and reactivity, potentially involving the formation of a dimsyl anion acting as an electron donor–acceptor complex with benzene, as previously observed by Laulhé during his light-promoted cross-coupling reactions. Additionally, N-allyl aniline 1af displayed reactivity similar to that of 4-phenylbutene 1s, undergoing isomerization over two positions to form an imine (observed by crude 1H NMR), which then hydrolyzed to deliver deallylated aniline 2af. On the basis of these observations, additional studies are provided in SI (Tables S3–S7) to further confirm the power of the divergent reactivity patterns and highlight the role of KO t Bu in DMSO.

Conclusion

This article reports a straightforward isomerization of miscellaneous alkenes. The method is applicable for a wide range of substrates, including allylic derivatives of benzenes, aromatic and aliphatic systems, heterocycles, ethers, thioethers, amines, and sulfones, while dienes are also expected to be compatible. When the standard reaction conditions were unproductive, increasing the amount of KO t Bu, temperature, or reaction time, the adducts were successfully obtained. Furthermore, this methodology provided more than 30 adducts from commercial starting material, all potential building blocks in the synthesis of valuable materials. Therefore, this versatile procedure could be utilized for a myriad of substrates and diverse molecular targets, including ketones and deallylation strategies.

Supplementary Material

ao6c00595_si_001.pdf (4.1MB, pdf)

Acknowledgments

We are grateful to FGCU and the Seidler Funds for partially supporting this work. We also thank Tobias Pedro for aiding during the synthesis of a few substates. This original research article was mainly supported by the National Institute of General Medical Sciences (NIGMS) of the National Institutes of Health (NIH) under award number 1R15GM141726-01. Furthermore, this work is dedicated to Alena Bugarin.

The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.6c00595.

  • Detailed experimental procedures and copies of 1H NMR and 13C NMR spectra for all of the compounds (PDF)

†.

Department of Forensic Science, Sam Houston State University, Huntsville, TX 77340, United States

‡.

Department of Chemistry, Florida International University, Miami, FL, 33199, United States

§.

División Académica de Ciencias Básicas, Universidad Juárez Autónoma de Tabasco, Carretera Cunduacán-Jalpa Km. 0.5, Cunduacán 86690, Mexico

The authors declare no competing financial interest.

Due to a production error, the header rows were missing from Tables 2−5 in the version of this article that was published ASAP March 10, 2026. The corrected version was posted March 12, 2026.

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