. 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 4.

Effect of Bases in the Ethylene–Benzaldehyde Coupling ^a


entry	base	yield ^b
1	Et₃N	77
2	Et₂NH	3
3	N-methylpyrrolidine	36
4	proton sponge	10
5	pyridine	12
6 ^c	K₃PO₄	<5
7	K₃CO₃	<5
8	Cs₂CO₃	<5

Standard procedure: Ni(cod)₂ (20 mol%) and (o-anisyl)₃P (40 mol%) were dissolved in 2.5 mL toluene under argon. Ethylene (balloon, 1atm) was substituted for argon. A base (600 mol%), benzaldehyde (100 mol%, 0.5 mmol), and Et₃SiOTf (175 mol%) were added. The reaction mixture was stirred 18 h at 23 °C.

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

Benzaldehyde was replaced by 2-naphthaldehyde and the reaction was run at 0.25 mmol scale.