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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 1.

Halide Inhibition in Conjunctive Coupling.a

graphic file with name nihms875951u2.jpg
entry alteration yieldb erc
1 none 77 98:2
2 1% LiI 13 98:2
3 1% LiBr 41 98:2
4 1% LiCl 40 98:2
5 1% (n-Bu)4NCl 31 98:2
6 1% LiI, 5% catalyst 69 98:2
7 PhCl instead of PhOTf <5 nd
8 PhBr instead of PhOTf 9 96:4
9 PhI instead of PhOTf 9 96:4
10 100% LiBr 23 22:78
11 100% n-Bu4NBr 19 92:8
a

The "ate" complex was prepared by addition of n-butyllithium to vinylB(neo) 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.