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. Author manuscript; available in PMC: 2016 Mar 20.
Published in final edited form as: Org Lett. 2015 Mar 6;17(6):1493–1496. doi: 10.1021/acs.orglett.5b00381

Table 1.

Optimization study

graphic file with name nihms674744t1.jpg
entry L•HX temp
(°C)		 R C
mM		 rra
(5:6)		 NMRb
yield %		 isolated
yield %
1 DP-IPr rt Et 3 93:7 - 21
2 DP-IPr 90 Et 3 - trace -
3 DP-IPr 90 i-Pr 3 - trace -
4 SIPr 90 i-Pr 3 >95:5 27 -
5 IPr 90 i-Pr 3 >95:5 18 -
6 IPrMe 90 i-Pr 3 >95:5 35 -
7 IPrCl 90 i-Pr 3 >95:5 67 66
8 IPrCl 50 i-Pr 3 >95:5 30 -
9 IPrCl 90 i-Pr 5 >95:5 - 69
10 IPrCl 90 i-Pr 10 >95:5 32 -
11 IPrCl 90 Et 5 65:35 - 51c
12d IPrCl 90 i-Pr 5 >95:5 17 -
13e IPrCl 90 i-Pr 5 >95:5 - 63
graphic file with name nihms674744t2.jpg
a

Determined by 1H-NMR analysis of the crude mixture.

b

1,3,5-trimethoxybenzene was used as internal standard. Preparative experiments were not conducted with an internal standard due to complexity of removing the internal standard.

c

Combined yield.

d

Ni(COD)2 (23 mol %), IPrCl•HCl (20 mol %), KO-t-Bu (24 mol %).

e

Ni(COD)2 (43 mol %), IPrCl•HCl (40 mol %), KO-t-Bu (44 mol %).