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. 2021 Mar 24;143(13):4903–4909. doi: 10.1021/jacs.1c01022

Table 1. Reaction Optimizationa.

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entry PC NHCb sulfinate base (equiv) yield of 3a (%)c
1 PC-I A PhSO2Na Cs2CO3 (2) n.d.
2 PC-I A PhSO2Na KOtBu (2) n.d.
3 PC-I A PhSO2Na DBU (2) n.d.
4 PC-I A PhSO2Na Cs2CO3 (1) + KOtBu (1) trace
5 PC-I A PhSO2Na Cs2CO3 (1) + DBU (1) 8
6 PC-I A PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 26
7 PC-I B PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 39
8 PC-I C PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 17
9 PC-I D PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 22
10 PC-II B PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 43
11 PC-III B PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 28
12 PC-IV B PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 35
13 PC-V B PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) n.d.
14 PC-II B 4-OMe-PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 10
15 PC-II B 4-Cl-PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 56
16 PC-II B 4-CN-PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 48
17 PC-II B MeSO2Na Cs2CO3 (0.5) + MTBD (1.3) 4
18 PC-II B 4-Cl-PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) 81 (78)d
19 PC-II B 4-Cl-PhSO2Na Cs2CO3 (0.5) + MTBD (1.3) n.d.e
a

Reaction conditions: 1a (0.15 mmol), 2a (0.3 mmol), NHC (15 mol %), photoredox catalyst (1.5 mol %), PhSO2Na (25 mol %), base (2.0 equiv), and MeCN (1.5 mL) under irradiation with a 23 W CFL for 24 h.

b

Photoredox catalysts and NHCs:b

c

GC yields using biphenyl as an internal standard. The yield of the isolated product is given in parentheses.

d

20 mol % NHC, 30 mol % 4-Cl-PhSO2Na, and 2.5 equiv of 2a were applied.

e

Without photoredox catalyst, NHC, sulfinate, or irradiation.