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. 2014 Aug 26;79(17):8296–8303. doi: 10.1021/jo5015432

Table 1. Optimization of Reaction Conditionsa.

graphic file with name jo-2014-015432_0007.jpg

entry catalyst (mol %) time (h) temperature (°C) 1a:2a yield (%)c
1b [Cp*RhCl2]2 (5)/AgSbF6 (20) 24 110 1:2 20
2b [Cp*RhCl2]2 (5) 24 110 1:2 0
3b AgSbF6 (20) 24 110 1:2 29
4 FeCl3 (20) 24 rt 1:2 31
5 AlCl3 (20) 24 rt 1:2 0
6 BF3·Et2O (40) 24 rt 1:2 15
7 BF3·Et2O (20) 24 rt 1:2 22
8 BF3·Et2O (10) 24 rt 1:2 32
9 BF3·Et2O (5) 24 rt 1:2 29
10 BF3·Et2O (10) 48 rt 1:2 40
11 BF3·Et2O (10) 48 reflux 1:2 63
12 BF3·Et2O (10) 48 reflux 2:1 70
13d BF3·Et2O (10) 48 reflux 2:1 79e
a

Conditions: 0.40 mmol limiting reagent in CH2Cl2 (0.05 M), in glovebox.

b

DCE as solvent.

c

Determined by GC relative to tetradecane as an internal standard.

d

Conditions: 1a (2.0 mmol) and 2a (1.0 mmol) in CH2Cl2 (0.05 M), outside glovebox.

e

Isolated yield.