Nickel-catalyzed electrochemical couplings of vinyl halides: Synthetic andstereochemical aspects

Citation
C. Cannes et al., Nickel-catalyzed electrochemical couplings of vinyl halides: Synthetic andstereochemical aspects, J ORG CHEM, 65(15), 2000, pp. 4575-4583
Citations number
78
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
15
Year of publication
2000
Pages
4575 - 4583
Database
ISI
SICI code
0022-3263(20000728)65:15<4575:NECOVH>2.0.ZU;2-V
Abstract
Homo- and cross-coupling involving alkenyl halides have been performed effi ciently using an electroassisted nickel-complex catalysis. Valuable product such as conjugated dienes, beta,gamma- or gamma,delta-unsaturated eaters, ketones, or nitriles, as well as alkenylated aryl compounds are thus prepar ed with high yields and high stereoselectivity. Partial isomerization is on ly observed in a few cases, when the alkenyl halide is involved in a late s tep of the catalytic cycle. This is the case in the preparation of (Z,Z)-1, 3-diene.