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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 3.

Ni-catalyzed Borylation of Heteroaryl Bromides with BBA

graphic file with name nihms495850t23.jpg
entry product time temperature yield (%)
1 graphic file with name nihms495850t24.jpg 3a 4 h rt 94
2a graphic file with name nihms495850t25.jpg 3b 4 h rt 85
3a graphic file with name nihms495850t26.jpg 3c 6 h rt 74
4 graphic file with name nihms495850t27.jpg 3d 4 h rt 92
5 graphic file with name nihms495850t28.jpg 3e 4 h rt 91
6b graphic file with name nihms495850t29.jpg 3f 12 h rt 82
7 graphic file with name nihms495850t30.jpg 3g 6 h rt 86
8b graphic file with name nihms495850t31.jpg 3h 4 h 80 °C 72
9b graphic file with name nihms495850t32.jpg 3i 4 h 80 °C 74
10b graphic file with name nihms495850t33.jpg 3j 4 h 80 °C 81
11b graphic file with name nihms495850t34.jpg 3k 4 h 80 °C 83
12b graphic file with name nihms495850t35.jpg 3l 4 h 80 °C 83
a

NiCl2(dppp) (0.5 mol %), PPh3 (1 mol %)

b

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