TY - JOUR
T1 - Synthesis of functionalized benzylsilanes from arylzinc compounds and (iodomethyl)trimethylsilane by means of a novel Rh catalysis
AU - Takahashi, Hideki
AU - Hossain, Kabir M.
AU - Nishihara, Yasushi
AU - Shibata, Takanori
AU - Takagi, Kentaro
PY - 2006/1/20
Y1 - 2006/1/20
N2 - 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.
AB - 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.
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U2 - 10.1021/jo0520994
DO - 10.1021/jo0520994
M3 - Article
C2 - 16408978
AN - SCOPUS:30744458871
SN - 0022-3263
VL - 71
SP - 671
EP - 675
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -