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. Author manuscript; available in PMC: 2011 Aug 1.
Published in final edited form as: J Am Chem Soc. 2006 Sep 6;128(35):11513–11528. doi: 10.1021/ja062866w

Table 7.

Examination of Other Nickel Precatalysts a

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entry catalyst yield (2b) b yield (2b′) b ratio (2b:2b′) c combined yield b (2b+2b′)
1 Ni(cod)2/Ph3P 78% 6% 93:7 84%
2 Ni(Ph3P)4 41% 3% 93:7 44%
3 Ni(acac)2/Ph3P/DIBAL-H 72% 5% 93:7 77%
4 Ni(Ph3P)2Cl2/n-BuLi 32% 2% 94:6 34%
5 Ni(Ph3P)2Br2/n-BuLi <5% <5% n.d. <5%
a

Standard procedure: The nickel precatalyst system (20 mol%) was dissolved in 2.5 mL toluene. The alkene (1 mL), triethylamine (600 mol%), the aldehyde (100 mol%, 0.5 mmol), and Et3SiOTf (175 mol%) were added. The reaction mixture was stirred 48 h at 23 °C.

b

Yields were determined by 1H NMR using DMF as a standard.

c

Ratios were determined by 1H NMR of the crude reaction mixture.