Skip to main content
. Author manuscript; available in PMC: 2020 Oct 18.
Published in final edited form as: Org Lett. 2019 Sep 27;21(20):8290–8294. doi: 10.1021/acs.orglett.9b03053

Table 1.

Optimization of Radical Addition Reaction

graphic file with name nihms-1060711-t0008.jpg
entry Lewis acid (2 equiv) silicate (equiv) solvent time (h) % conva
1 none 2 DMSO 24 40
2 none 2 DMSO 49 48
3 ZnBr2 1 DMSO 18 27
4 Zn(OTf)2 1 DMSO 18 27
5 ZnBr2 2 DMSO 18 63
6 ZnBr2 4 DMSO 18 64
7 ZnBr2 (3 equiv) 2 DMSO 18 49
8 MgCl2 2 DMSO 18 59
9 MgBr2 2 DMSO 18 54
10 Mg(OTf)2 2 DMSO 18 31
11 ZnBr2 2 DMF 16 28
12 MgCl2 2 DMF 16 44
13 MgCl2 1.2 EtOH 23 10
14 MgCl2 2.6 DMSO 48 86
15 MgCl2 3 DMSO 48 22b
16 MgCl2 3 DMSO 48 68c
17d MgCl2 3 DMSO 47 88 (60e)
18 MgCl2 2 DMSO 24 73
a

Determined by 1H NMR integration.

b

1 mol % of catalyst loading.

c

5 mol % of catalyst loading.

d

Conversions in control experiments using conditions of entry 17: Absence of blue LED (0%), absence of 4CzIPN (0%), open to air (67%), replacing silicate with CyBF3K (59%).

e

Isolated yield.