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. Author manuscript; available in PMC: 2020 Feb 13.
Published in final edited form as: J Am Chem Soc. 2019 Jan 30;141(6):2257–2262. doi: 10.1021/jacs.9b00111

Table 1.

Reaction Optimizationa

graphic file with name nihms-1008619-t0007.jpg
entry [Ni] ligand yield (%)b
1c NiCl2·DME ttbtpy 68
2 NiCl2·DME ttbtpy 75
3 NiCl2·DME tpy 47
4 NiCl2·DME phen 14
5 NiCl2·DME dtbbpy 15
6 NiCl2·DME 1-bpp 49
7 NiCl2·6H2O ttbtpy 20
8 Ni(acac)2·xH2O ttbtpy 81
9d Ni(acac)2·xH2O ttbtpy 80
10 none ttbtpy 3
11 Ni(acac)2·xH2O none 9
graphic file with name nihms-1008619-t0008.jpg
12 NiCl2·DME ttbtpy 18
13 NiCl2·DME tpy 68
14 NiCl2·DME 1-bpp 83
a

Conditions: Pyridinium salt 1a (0.1 mmol), [Ni] (10 mol %), ligand (12 mol %), AlkZnBr (1.6 equiv), THF/DMA (2:1, 0.2 M), 60 °C, 16–22 h, unless noted otherwise.

b

Determined by 1H NMR spectroscopic analysis using 1,3,5-trimethoxybenzene as internal standard.

c

AlkZnBr (1.4 equiv).

d

5 mol % [Ni], 6 mol % ligand.