Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 346, Issue 13-15, Pages 1674-1678Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200404192
Keywords
alkyl tosylates; allyl ethers; carbon-carbon bond formation; carbon-silicon bond formation; chlorosilanes; Grignard reagents; nickel
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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 pi-allyl-nickel complexes with the vinyl-Grignard reagent and subsequent trapping of the thus formed allyl-Grignard reagents with electrophiles is proposed.
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