論文

査読有り
2016年6月

C-H Activation Induced by Oxidative Addition of N-O Bonds in Oxime Esters: Formation of Rhodacycles and Cycloaddition with Alkynes

ORGANOMETALLICS
  • Takuya Shimbayashi
  • ,
  • Kazuhiro Okamoto
  • ,
  • Kouichi Ohe

35
11
開始ページ
2026
終了ページ
2031
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1021/acs.organomet.6b00311
出版者・発行元
AMER CHEMICAL SOC

The reaction of oxime esters with a rhodium(I) precursor to form five-membered rhodacycles via N-O bond cleavage followed by C-H bond activation has been investigated by isolating these complexes. Kinetic studies on the formation of rhodacycles show that the reversible oxidative addition of the N-O bond in the oxime ester to RhCl(PPh3)(3) occurs at room temperature. The E-isomer of the oxime ester was found to undergo rhodacycle formation faster than the Z-isomer, which suggests that the geometry of the oxime esters reflects the geometry of intermediates during C-H activation. The rhodacycle reacted with an alkyne to construct an isoquinoline ring in both stoichiometric and catalytic conditions, despite its basic stability in air, in moisture, and even during heating, which demonstrates the potential of the rhodacycle as an intermediate for further catalytic transformation of oxime esters.

Web of Science ® 被引用回数 : 7

リンク情報
DOI
https://doi.org/10.1021/acs.organomet.6b00311
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000377925600052&DestApp=WOS_CPL

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