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. Author manuscript; available in PMC: 2018 Nov 22.
Published in final edited form as: Angew Chem Int Ed Engl. 2018 Sep 3;57(40):13106–13109. doi: 10.1002/anie.201806963

Table 1.

Site-specific C–H dithiocarbamylation of simple substrates.[a]

entry product blue LEDs yield (%)[b] radical initiator yield (%)[c]
graphic file with name nihms-994687-t0006.jpg
1 1: R = iPr 91 73
2 2: R = tBu 61 56
3 3: R = nPr 79 (3:1 C4:C5) 85 (3:1 C4:C5)
4 4: R = nHex 87 (2.5:1 rr)[d] 87 (1.6:1 rr)[d]
graphic file with name nihms-994687-t0007.jpg
5 5: R = Ph 82 82
6 6: R = CF3 78 86
7 graphic file with name nihms-994687-t0008.jpg 65 76
8 graphic file with name nihms-994687-t0009.jpg 21 (35% brsm) 52
9 graphic file with name nihms-994687-t0010.jpg 89 (2:1 dr) 79 (2:1 dr)
10 graphic file with name nihms-994687-t0011.jpg 81 (2:1 dr) 87 (2:1 dr)
[a]

Isolated yields.

[b]

Reactions were performed with blue LEDs in PhCF3 under ambient conditions for 14 h under Ar

[c]

Reactions were performed in PhCl at 120 °C with 10 mol % dicumyl peroxide for 14 h under Ar

[d]

Regioisomeric mixture resulting from 1,5-functionalization of the amide sidechain.