Thioamide‐Directed Cobalt(III)‐Catalyzed Selective Amidation of C(sp<sup>3</sup>)−H Bonds

DOI Web Site Web Site 被引用文献12件
  • Peng Wen Tan
    Organic Chemistry Institute of Chemical and Engineering Sciences 8 Biomedical Grove, Neuros, #07-01 Singapore 138665 Singapore
  • Adrian M. Mak
    Institute of High Performance Computing 1 Fusionopolis Way #16-16 Singapore 138632 Singapore
  • Michael B. Sullivan
    Institute of High Performance Computing 1 Fusionopolis Way #16-16 Singapore 138632 Singapore
  • Darren J. Dixon
    Department of Chemistry Chemistry Research Laboratory University of Oxford 12 Mansfield Road Oxford UK
  • Jayasree Seayad
    Organic Chemistry Institute of Chemical and Engineering Sciences 8 Biomedical Grove, Neuros, #07-01 Singapore 138665 Singapore

書誌事項

公開日
2017-11-30
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/anie.201709273
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>A mild, oxidant‐free, and selective Cp*Co<jats:sup>III</jats:sup>‐catalyzed amidation of thioamides with robust dioxazolone amidating agents via C(sp<jats:sup>3</jats:sup>)−H bond activation to generate the desired amidated products is reported. The method is efficient and allows for the C−H amidation of a wide range of functionalized thioamides with aryl‐, heteroaryl‐, and alkyl‐substituted dioxazolones under the Cp*Co<jats:sup>III</jats:sup>‐catalyzed conditions. The observed regioselectivity towards primary C(sp<jats:sup>3</jats:sup>)−H activation is supported by computational studies and the cyclometalation is proposed to proceed by means of an external carboxylate‐assisted concerted metalation/deprotonation mechanism. The reported method is a rare example of the use of a directing group other than the commonly used pyridine and quinolone classes for Cp*Co<jats:sup>III</jats:sup>‐catalyzed C(sp<jats:sup>3</jats:sup>)−H functionalization and the first to exploit thioamides.</jats:p>

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