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. Author manuscript; available in PMC: 2019 May 4.
Published in final edited form as: Angew Chem Int Ed Engl. 2018 Apr 6;57(19):5369–5373. doi: 10.1002/anie.201800749

Table 1.

Optimization of Lewis acid mediated C- vs O-arylation.a

graphic file with name nihms-1521646-t0005.jpg
entry addictive base %yield(alcohol/ether)b
1 none quinuclidine 3/54
2 ZnCl2 quinuclidine 44/0
3 ZnBr2 quinuclidine 48/0
4 ZnCl2 NaOH 66/0
5 ZnCl2 K3PO4 60/0
6 ZnBr2 K3PO4 52/0
7c,d,e ZnCl2 K3PO4 74/0
8c,d,e,f ZnCl2 K3PO4 65/0
graphic file with name nihms-1521646-t0006.jpg
a

Performed on a 10 µmol scale with photocatalyst 1 (0.5 mol%), NiBr2•Me4phen (0.5 mol%), quinuclidine (30 mol%), aryl halide (1.0 equiv.), alcohol (5.0 equiv.), additive (1.5 equiv.), base (1.0 equiv.) in DMSO (0.25 M).

b

Yield determined by UPLC or 1H NMR analysis.

c

Reaction conducted on 0.3 mmol scale

d

Photocatalyst (0.2 mol%), NiBr2•Me4phen (1.5 mol%).

e

Performed with photocatalyst 19.

f

3 equiv. of alcohol.