. 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 1.

Nickel-Catalyzed Coupling of Ethylene, Aldehydes, and Silyl Triflates


entry	R (aldehyde)	R₃SiOTf	product	isolated yield (%)
1	Ph	Et₃SiOTf	1a	82 (65) ^b
2	p-tolyl	Et₃SiOTf	1b	88 (65) ^b
3	o-tolyl	Et₃SiOTf	1c	93 (64) ^b
4	p-anisyl	Et₃SiOTf	1d	95 (65) ^c
5	2-naphthyl	Et₃SiOTf	1e	95 (83) ^b
6	2-naphthyl	Me₃SiOTf	1f	60
7	2-naphthyl	t-BuMe₂SiOTf	1g	67
8		Et₃SiOTf	1h	80
9	2-furyl	Et₃SiOTf	1i	38
10 ^f		Et₃SiOTf	1j	25
11 ^f		Et₃SiOTf	1k	34
12	piv	Et₃SiOTf	1l	70
13		Et₃SiOTf	1m	81 (40) ^c, ^d
14	cyclohexyl	Et₃SiOTf	1n	25 ^d (34) ^d, ^e

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. Triethylamine (600 mol%), the aldehyde (100 mol%, 0.5 mmol), and Et₃SiOTf (175 mol%) were added. The reaction mixture was stirred 6–18 h at 23 °C.

(o-anisyl)₃P was replaced by Cy₂PhP.

(o-anisyl)₃P was replaced by Ph₃P.

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

Conducted under 2 atm of ethylene.

Stirred at room temperature for 30 h.