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. 2015 Feb 20;17(5):1256–1259. doi: 10.1021/acs.orglett.5b00241

Table 1. Optimization of Decarboxylative Cross-Coupling.

graphic file with name ol-2015-00241v_0007.jpg

entry X ligand temp (°C) yield of 1aa,b (%)
1 I PCy3HBF4 140 58
2 I PtBu3HBF4 140 79
3 I none 140 72
4c I PtBu3HBF4 140 0
5 Br none 140 6
6 Br PCy3HBF4 140 32
7 Br PtBu3HBF4 140 13
8 Br CM-Phos 140 55
9 Br CM-Phos 160 62
10c Br CM-Phos 160 0
11 Cl CM-Phos 140 31
12 Cl PtBu3HBF4 140 0
13 Cl PCy3HBF4 140 <2
14 Cl DPPF 140 51
15c Cl DPPF 140 0
a

General conditions: Ni(COD)2 (0.1 equiv), ligand (0.2 equiv), diglyme, 20 h.

b

Calibrated GC yields against hexadecane as the internal standard.

c

General conditions but with no Ni(COD)2.