Novel carbon-carbon bond formation through Mizoroki-Heck type reaction of silanols and organotin compounds

Kazunori Hirabayashi, Jun Ichi Ando, Jun Kawashima, Yasushi Nishihara, Atsunori Mori, Tamejiro Hiyama

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

The reaction of dimethyl(phenyl)silanol with butyl acrylate in the presence of a stoichiometric amount of Pd(OAc)2 or by a combined use of 0.1 molar amount of Pd(OAc)2 and Cu(OAc)2/LiOAc (molar ratio 3/2) gave butyl cinnamate in 76% or 57% yield, respectively. The similar reaction with tributyl(phenyl)tin also proceeded in 77% yield. The organotin compound was shown to react faster than the sitanol, although the tin reagent sometimes induced undesirable homocoupling, while the reaction with silanol did not give such by-product.

Original languageEnglish
Pages (from-to)1409-1417
Number of pages9
JournalBulletin of the Chemical Society of Japan
Volume73
Issue number6
DOIs
Publication statusPublished - Jun 2000
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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