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. Author manuscript; available in PMC: 2014 May 3.
Published in final edited form as: J Org Chem. 2013 Apr 17;78(9):4615–4619. doi: 10.1021/jo4005519

Table 1.

Borylation of Various Heterocyclic Halidesa

graphic file with name nihms470496u1.jpg
entry alkyl halide product yield (%)
1 graphic file with name nihms470496t1.jpg graphic file with name nihms470496t2.jpg
1a
72
2 graphic file with name nihms470496t3.jpg graphic file with name nihms470496t4.jpg
1b
51
3 graphic file with name nihms470496t5.jpg graphic file with name nihms470496t6.jpg
2
59
4 graphic file with name nihms470496t7.jpg graphic file with name nihms470496t8.jpg
3
54
5 graphic file with name nihms470496t9.jpg graphic file with name nihms470496t10.jpg
4a
27
6 graphic file with name nihms470496t11.jpg graphic file with name nihms470496t12.jpg
4a
52
7 graphic file with name nihms470496t13.jpg graphic file with name nihms470496t14.jpg
5
52
8 graphic file with name nihms470496t15.jpg graphic file with name nihms470496t16.jpg
6
30
a

Reaction conditions: Halide (1.0 equiv), B2pin2 (1.5 equiv), CuI (10 mol %), PS-PPh3 (13 mol %), MeOLi (2.0 equiv), DMF ([halide] = 0.2 M), rt, 20 h then sat. aq KHF2 (4.0 equiv), THF, rt, 2 h.