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. Author manuscript; available in PMC: 2012 Aug 5.
Published in final edited form as: Org Lett. 2011 Jul 8;13(15):3818–3821. doi: 10.1021/ol2010165

Table 1.

Effects of Catalyst and Additive on Z/E Ratios in 2a

graphic file with name nihms310694t1.jpg

entry catalyst 2 / 3 / 4b 2, Z / Ec
1 Pd(PPh3)4 39/31/30 98/2
2 PdCl2(PPh3)2 53/32/15 98/2
3 PdCl2 + 3P(2-Fur)3 80/3/17 98/2
4 PdCl2 + 3P(2-Tol)3 96/2/2 99/1
5 PdCl2(Amphos)2d 88/<1/12 68/32
6 Pd[P(t-Bu)3]2 38/26/36 73/27
7 PdCl2(PCy3)2 95/4/1 33/67
8 PEPPSI 55/33/12 45/55
9 PdCl2(PCy3)2 + 3PPh3 73/9/18 98/2
10 PdCl2(PPh3)2 + TMEDAe 99/<1/<1 >99/1
11 PdCl2(PPh3)2 + Et3Nf 79/5/16 98/2
a

Conditions: alkylzinc iodide (1.1 mmol, 1.0 M in THF), vinyl iodide (1 mmol), Pd catalyst (2 mol %). Reactions were run at 0.33 M at rt, 4 h (24 h for entries 10 and 11).

b

by GC.

c

Z/E-ratio determined by NMR or GC on crude material.

d

Defined as dichloro-bis(p-dimethylaminophenyl-di-tert-butylphosphine) palladium(II).

e

1.1 equiv.

f

2.2 equiv.