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. Author manuscript; available in PMC: 2013 Sep 21.
Published in final edited form as: Org Lett. 2012 Sep 4;14(18):4814–4817. doi: 10.1021/ol302124j

Table 2.

Trifluoroborate Synthesis from Heteroaryl Chlorides and Bromides

graphic file with name nihms405477u3.jpg
entry X product time (h) % isolated Yield
1 Cl graphic file with name nihms405477t19.jpg 6 45
2 Cl graphic file with name nihms405477t20.jpg 5 5
3 Cl graphic file with name nihms405477t21.jpg 11 58, 47a
4 Br graphic file with name nihms405477t22.jpg 5.5 37, 85a
5 Br graphic file with name nihms405477t23.jpg 4.5 96, 93a
6 Br graphic file with name nihms405477t24.jpg 6 70
7 Cl graphic file with name nihms405477t25.jpg 5 36, 81a
8 Br graphic file with name nihms405477t26.jpg 5 64, 68a

General conditions: 0.5 mol % of 1, 1.0 mol % of 2, 3.0 equiv of KOAc, 3.0 equiv of B2(NMe2)4, MeOH (0.2 M), 60 °C for time indicated.

a

Yield from previous method with B2(OH)4 as boron source (ref 15).