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Novel Nickel‐Catalyzed Coupling Reaction of Allyl Ethers with Chlorosilanes, Alkyl Tosylates, or Alkyl Halides Promoted by Vinyl‐Grignard Reagent Leading to Allylsilanes or Alkenes
Author(s) -
Terao Jun,
Watabe Hiroyasu,
Watanabe Hiroyuki,
Kambe Nobuaki
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404192
Subject(s) - chemistry , alkyl , reagent , transmetalation , catalysis , electrophile , halide , organic chemistry , medicinal chemistry , grignard reaction , nickel , polymer chemistry
A new method for a carbon‐silicon or carbon‐carbon bond forming reaction between allyl ethers and chlorosilanes, alkyl tosylates, or alkyl halides giving rise to allylsilanes or alkenes has been developed. This reaction proceeds efficiently at ambient temperature by the combined use of nickel catalysts and a vinyl‐Grignard reagent. A possible reaction pathway involving the formation of allyl‐Grignard reagents via transmetallation of π‐allylnickel complexes with the vinyl‐Grignard reagent and subsequent trapping of the thus formed allyl‐Grignard reagents with electrophiles is proposed.