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. Author manuscript; available in PMC: 2016 Jun 3.
Published in final edited form as: Tetrahedron Lett. 2014 Dec 20;56(23):3306–3310. doi: 10.1016/j.tetlet.2014.12.076

Table 1.

The nature of the ligand and borane affect the distribution of borylated products and their derived alcohols.a

graphic file with name nihms651265t1.jpg
entry 5 R = L borane 6 (er) 7 8
1 a Me L1 tmdBH 6 (56:44) 56 30
2 a Me L2 tmdBH 58 (67:34) 31 10
3b a Me L2 pinBH 30 (56:44) 16 24
4 a Me L2 catBH 63 (53:47) 1 6
5 b iBu L2 tmdBH 52 (80:20) 29 16
6 b iBu L2 catBH 16 (50:50) 0 0
7 c cC6H11 L2 tmdBH 60 (70:30) 11 28
8 c cC6H11 L2 catBH 52 (85:15) 2 5
a

Reaction conditions: 2% [(L)2Rh(nbd)]BF4, 2 equiv. borane, THF, rt.

b

16% of the isomeric β-hydroxy isomer also formed.