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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 1.

Ni-catalyzed Borylation of Electron-Rich and Electron-Neutral Aryl Bromides with BBA

graphic file with name nihms495850t1.jpg
entry product time temperature yield (%)
1 graphic file with name nihms495850t2.jpg 1a 2 h 80 °C 91
2 graphic file with name nihms495850t3.jpg 1b 2 h 80 °C 89
3 graphic file with name nihms495850t4.jpg 1c 2 h 80 °C 77
4a graphic file with name nihms495850t5.jpg 1d 6 h rt 78
5a graphic file with name nihms495850t6.jpg 1e 6 h rt 67
6 graphic file with name nihms495850t7.jpg 1f 4 h 80 °C 84
7 graphic file with name nihms495850t8.jpg 1g 3 h 80 °C 72
8 graphic file with name nihms495850t9.jpg 1h 6 h rt 90
9 graphic file with name nihms495850t10.jpg 1i 4 h rt 93
10 graphic file with name nihms495850t11.jpg 1j 4 h
8 h
rt 90
81b
a

3 mol % NiCl2(dppp) and 6 mol % PPh3

b

48 mmol scale using 0.1 mol % NiCl2(dppp), 0.2 mol % PPh3 in EtOH (90 mL)