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. Author manuscript; available in PMC: 2018 Aug 17.
Published in final edited form as: Adv Synth Catal. 2017 Jul 12;359(16):2890–2894. doi: 10.1002/adsc.201700438

Table 1.

Optimization of α-arylation of azaarylmethylamine 1a with ArCl 2b.a, b

graphic file with name nihms921195u2.jpg
Entry NiBr2/L (mol %) Conc. (M) Temp (°C) Assay yield (%)
1 5/7.5 0.1 110 97
2 2.5/3.75 0.1 110 95(22c)
3 1/1.5 0.1 110 43
4 2.5/3.75 0.1 80 75
5 2.5/3.75 0.05 110 76
6 2.5/3.75 0.2 110 80
a

Reactions conducted on a 0.1 mmol scale using 1 equiv of 1a, 2 equiv of LiN(SiMe3)2, and 1.2 equiv of ArCl.

b

Yields determined by 1H NMR spectroscopy of the crude reaction mixtures on a 0.1 mmol scale.

c

1 equiv. of LiN(SiMe3)2.