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. 2019 Aug 2;84(17):11316–11322. doi: 10.1021/acs.joc.9b01753

Table 1. Reaction Optimization.

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no.a solvent 4a:5a ratio other yield (%)
1 toluene 1:2   50
2 n-hexane 1:2   24
3 CHCl3 1:2   68
4 DCM 1:2   80
5 1,2-DCE 1:2   73
6 EtOAc 1:2   67
7 CH3CN 1:2   69
8 THF 1:2   67
9 DCM 1:4   60
10 DCM 1:1   76
11 DCM 2:1   55
12b DCM 1:2 slow add. 83
13 DCM 1:2 0.5 mL 76
14 DCM 1:2 2 mL 71
15c DCM 1:2 dark no reaction
a

Reaction conditions: 4a (0.4 mmol) and 5a (0.8 mmol) were dissolved in 1 mL of solvent and were irradiated at room temperature with blue LEDs (1 W, 470 nm) overnight (16 h).

b

4a and 5a were each dissolved in 0.5 mL of DCM, 5a being slowly added over the course of 6 h by a syringe pump, under otherwise identical conditions.

c

The reaction mixture was stirred in the dark.