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. Author manuscript; available in PMC: 2012 Jun 3.
Published in final edited form as: J Org Chem. 2011 Apr 29;76(11):4697–4702. doi: 10.1021/jo200360s

TABLE 1. Optimizing Reaction Conditions.

graphic file with name nihms293196u3.jpg

entry CuX solventa conversion (%)b
1 CuCN CH2CI2 24
2 CuOAc CH2CI2 <5
3 Cu(OTf)2 CH2CI2 0
4 Cu(BF4)2 CH2CI2 15
5 Cu(NO3)2 CH2CI2 0
6 Cu(CIO4)2 CH2CI2 22
7 Cu(CF3COO)2 CH2CI2 0
8 Cu(CH3CN)4PF6 CH2CI2 27
9 CuCI CH2CI2 35
10 CuBr CH2CI2 43
11 CuI CH2CI2 64
12 - CH2CI2 45
13c CuI CH2CI2 63
14d CuI CH2CI2 68
15 CuI Toluene 64
16 CuI THF 70
17 CuI Et2O 71
18e CuI Et2O 76
19f CuI Et2O 85
20f - Et2O 43
21g CuI Et2O >99 (98)h
a

Reaction run in 0.5 m solution.

b

Based on 1H NMR.

c

Using 6 mol % CuI.

d

Using 3 mol % Grubbs-2 and 6 mol % CuI.

e

Reaction run in 0.2 m solution.

f

Reaction run in 0.1 m solution.

g

At 35 °C for 3 h; without CuI; yield = 57%

h

Isolated yield.