論文

2004年12月

Cross-coupling of triallyl(aryl)silanes with aryl bromides and chlorides: An alternative convenient biaryl synthesis

ADVANCED SYNTHESIS & CATALYSIS
  • AK Sahoo
  • ,
  • T Oda
  • ,
  • Y Nakao
  • ,
  • T Hiyama

346
13-15
開始ページ
1715
終了ページ
1727
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1002/adsc.200404188
出版者・発行元
WILEY-V C H VERLAG GMBH

Cross-coupling of a diverse range of aryl bromides with triallyl(aryl)silanes is effective in the presence of PdCl2/PCy3 and tetrabutylammonium fluoride (TBAF) in DMSO-H2O to give various biaryls in good yields. It is worthwhile to note that the all-carbon-substituted arylsilanes, stable towards moisture, acid, and base and easily accessible, serve as a highly practical alternative to their aryl(halo)silane counterparts. A catalyst system consisting of [(eta(3)-C3H5)PdCl](2) and 2-[2,4,6-(i-Pr)(3)C6H2]-C6H4PCy2 and use of TBAF- 3 H2O in THF-H2O are effective especially for the cross-coupling with aryl chlorides. Both of the catalyst systems tolerate a broad spectrum of common functional groups. The high efficiency of reactions is presumably due to the ready cleavage of the allyl groups upon treatment with TBAF(.)3 H2O and an appropriate amount of water. Diallyl(diphenyl)silane also cross-couples with various aryl bromides and chlorides in good yields, whereas allyl(triphenyl)silane gives the cross-coupled products in only moderate yields. Through sequential cross-coupling of bromo-chlorobenzenes with different arylsilanes, a range of unsymmetrical terphenyls are accessible in good overall yields.

リンク情報
DOI
https://doi.org/10.1002/adsc.200404188
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000225985800027&DestApp=WOS_CPL
ID情報
  • DOI : 10.1002/adsc.200404188
  • ISSN : 1615-4150
  • Web of Science ID : WOS:000225985800027

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