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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 12.

Coupling of Oxygen-Containing Alkenes with Aldehydes a

graphic file with name nihms308266u11.jpg
entry R1 (alkene) R2 (aldehyde) ligand major product yield (%) b ratio (4:4′) b ratio (E:Z) c
1 graphic file with name nihms308266t62.jpg Ph Cy2PhP graphic file with name nihms308266t63.jpg
4d 		<5 n.d. -
(EtO)Ph2P graphic file with name nihms308266t64.jpg
4d′		 <5 n.d. n.d.
2 e graphic file with name nihms308266t65.jpg Ph Cy2PhP graphic file with name nihms308266t66.jpg
4e 		21 n.d. -
(EtO)Ph2P graphic file with name nihms308266t67.jpg
4e′		 <5 n.d. n.d.
3 graphic file with name nihms308266t68.jpg o-anisyl Cy2PhP graphic file with name nihms308266t69.jpg
4f 		44 d 73:27 -
4 e graphic file with name nihms308266t70.jpg o-anisyl (EtO)Ph2P graphic file with name nihms308266t71.jpg
4g 		66 7:93 50:50
a

Standard procedure: To a solution of Ni(cod)2 (0.1 mmol) and ligand (0.2 mmol) in toluene (2.5 mL) at 23 °C under Ar were added the alkene (2.5 mmol), triethylamine (3.0 mmol), the aldehyde (0.5 mmol), and Et3SiOTf (0.875 mmol). The mixture was stirred 48 h at room temperature and purified by chromatography (SiO2).

b

Determined by 1H NMR of the crude reaction mixture using DMF as a standard.

c

The ratio was determined by 1H NMR of the mixture of E and Z homoallylic alcohols after the silyl group of the coupling product was removed by TBAF.

d

Isolated yield.

e

1.5 mmol alkene was used.