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. Author manuscript; available in PMC: 2015 May 14.
Published in final edited form as: J Am Chem Soc. 2014 Apr 29;136(19):7092–7100. doi: 10.1021/ja502280w

Table 1.

Optimized Catalyst for Allyl-Allyl Couplings

graphic file with name nihms-635411-t0002.jpg
entry catalyst substrate CsF
(equiv)		 t (h) T (°C) yield
(%)b 		erc
1 5% Pd2(dba)3
10% L1 		1a 0 12 60 72 96:4
2 0.25% (R)−4 1a 0 8 60 0 -
3 0.1% (R)−4 1a 0.05 4 60 95 96:4
4d 0.1% (R)−4 1a 0.05 4 60 96 96:4
5 0.1% (R)−4 1b 3 5 rt 92 97:3
6e 2% Pd2(dba)3
4% L1 		2a 3 12 60 86 96:4
7e 0.25% (R)−4 2a 3 4 60 59 94:6
8e 0.25% (R)−4 2b 5 5 rt 85 98:2

a The linear isomer of chloride was used.

b

Yield of purified material, average of two or more experiments.

c

Enantiomer ratios were determined by GC analysis on a chiral stationary phase and are an average of two or more experiments.

d

Reaction set up on benchtop and purged with N2.

e

Reaction run in 10:1 THF/H2O.