Synthesis of functionalized benzylsilanes from arylzinc compounds and (iodomethyl)trimethylsilane by means of a novel Rh catalysis

Hideki Takahashi; Kabir M Hossain; Yasushi Nishihara; Takanori Shibata; Kentaro Takagi

doi:10.1021/jo0520994

Synthesis of functionalized benzylsilanes from arylzinc compounds and (iodomethyl)trimethylsilane by means of a novel Rh catalysis

J Org Chem. 2006 Jan 20;71(2):671-5. doi: 10.1021/jo0520994.

Authors

Hideki Takahashi¹, Kabir M Hossain, Yasushi Nishihara, Takanori Shibata, Kentaro Takagi

Affiliation

¹ Department of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700-8530, Japan.

PMID: 16408978
DOI: 10.1021/jo0520994

Abstract

[reaction: see text] The catalytic activity of a Rh complex in cross-coupling between ArZnI and TMSCH2I was examined in which the Rh complex, generated in situ from [RhCl(1,5-cyclooctadiene)]2 and 1,1'-bis(diphenylphosphino)ferrocene, exhibited excellent catalytic activity for the production of various functionalized benzylsilanes in good yields. From 31P NMR studies of various solutions containing several of the reaction components, confirmation of the rapid and quantitative transfer of aryl groups from ArZnI to the Rh complex to form arylrhodium species was ascertained. A catalytic cycle, commencing with the transmetalation, was thus proposed for the reaction.