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. Author manuscript; available in PMC: 2014 Jul 5.
Published in final edited form as: J Org Chem. 2013 Jun 18;78(13):6427–6439. doi: 10.1021/jo401104y

Table 5.

Ni-catalyzed Borylation of Aryl and Heteroaryl Chlorides with BBA

graphic file with name nihms495850t42.jpg
entry Product time temperature yield (%)
1 graphic file with name nihms495850t43.jpg 2a 4 h rt 92
2 graphic file with name nihms495850t44.jpg 2c 4 h rt 89
3 graphic file with name nihms495850t45.jpg 2e 4 h 80 °C 89
4 graphic file with name nihms495850t46.jpg 5a 12 h rt 64
5a graphic file with name nihms495850t47.jpg 5b 8 h 80 °C 52
6 graphic file with name nihms495850t48.jpg 2i 12 h rt 83
7 graphic file with name nihms495850t49.jpg 1a 12 h 80 °C 66
8 graphic file with name nihms495850t50.jpg 5c 2 h 80 °C 69
9a graphic file with name nihms495850t51.jpg 3j 12 h 80 °C 75
10a graphic file with name nihms495850t52.jpg 3i 12 h 80 °C 58
11 graphic file with name nihms495850t53.jpg 3a 12 h rt 86
a

NiCl2(dppp) (5 mol %), PPh3 (10 mol %)