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. Author manuscript; available in PMC: 2018 Mar 1.
Published in final edited form as: J Am Chem Soc. 2017 Feb 16;139(8):3153–3160. doi: 10.1021/jacs.6b12663

Table 3.

Effect of solvent on catalytic conjunctive coupling reactions.a

graphic file with name nihms875951u3.jpg
entry RM Ar solvent yieldb erc
1 3-butenyl Ph THF <5% n/a
2 3-butenyl Ph THF/DMSO 73 91:9
3 Ph Ph THF 72 94:6
4 Ph Ph THF/DMSO 81 96:4
5 Ph p-MeO-Ph THF 78 92:8
6 Ph p-MeO-Ph THF/DMSO 89 98:2
7 Ph p-CF3-Ph THF 67 75:25
8 Ph p-CF3-Ph THF/DMSO 85 95:5
a

Reactions conducted as described in the text (see SI for additional details) and the conjunctive coupling was conducted at 0.17 M.

b

Yield represents isolated yield of purified material.

c

Enantiomer ratio (er) determined by chiral SFC analysis of boronic ester.