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

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Abstract

The catalytic activity of a Rh complex in cross-coupling between ArZnI and TMSCH2l 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.

Original languageEnglish
Pages (from-to)671-675
Number of pages5
JournalJournal of Organic Chemistry
Volume71
Issue number2
DOIs
Publication statusPublished - Jan 20 2006

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ASJC Scopus subject areas

  • Organic Chemistry

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