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. Author manuscript; available in PMC: 2024 Feb 15.
Published in final edited form as: J Am Chem Soc. 2023 Feb 1;145(6):3294–3300. doi: 10.1021/jacs.2c12767

Table 1.

Optimization and Control Studiesa

graphic file with name nihms-1875978-t0004.jpg
Entry Deviation Yield
2 (%)b 		Ar-H
3 (%)b
1 none 66 92
2 2 equiv Br1 58 99
3 Br2 instead of Br1 63 (61)c /
4 no base 27 48
5 Ni(cod)2 instead of NiCl2(H2O)6 59 86
6 no Ni/dtbbpy 0 21
7 in the dark 0 0
8 no photocatalyst 0 2
9 no aryl bromide 0 /
graphic file with name nihms-1875978-t0005.jpg
a

Optimizations were performed on a 0.2 mmol scale.

b

GC-MS yield with 1,3,5-trimethoxybenzene as external standard.

c

Yield in bracket refers to isolated amine products after subsequent one-pot Boc protection with NEt3 (2 equiv) and Boc2O (1 equiv) followed by purification using flash chromatography.