中国化学快报(英文版)2024,Vol.35Issue(9) :150-154.DOI:10.1016/j.cclet.2024.109495

Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings

Kun Tang Fen Su Shijie Pan Fengfei Lu Zhongfu Luo Fengrui Che Xingxing Wu Yonggui Robin Chi
中国化学快报(英文版)2024,Vol.35Issue(9) :150-154.DOI:10.1016/j.cclet.2024.109495

Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings

Kun Tang 1Fen Su 1Shijie Pan 1Fengfei Lu 1Zhongfu Luo 1Fengrui Che 1Xingxing Wu 1Yonggui Robin Chi2
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作者信息

  • 1. National Key Laboratory of Green Pesticide,Key Laboratory of Green Pesticide and Agricultural Bioengineering,Ministry of Education,Guizhou University,Huaxi District,Guiyang 550025,China
  • 2. National Key Laboratory of Green Pesticide,Key Laboratory of Green Pesticide and Agricultural Bioengineering,Ministry of Education,Guizhou University,Huaxi District,Guiyang 550025,China;School of chemistry,Chemical Engineering,and Biotechnology,Nanyang Technological University,Singapore 637371,Singapore
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Abstract

Enones are widely explored in synthetic chemistry as fundamental building blocks for a wide range of reactions and exhibit intriguing biological activities that are pivotal for drug discovery.The development of synthetic strategies for highly efficient preparation of enones thereby receives intense attention,in par-ticular through the transition metal-catalyzed coupling reactions.Here,we describe a carbene-catalyzed cross dehydrogenative coupling(CDC)reaction that enables effective assembly of simple aldehydes and alkenes to afford a diverse set of enone derivatives.Mechanistically,the in situ generated aryl radical is pivotal to"activate"the alkene by forming an allyl radical through intermolecular hydrogen atom transfer(HAT)pathway and thus forging the carbon-carbon bond formation with aldehyde as the acyl synthon.Notably,our method represents the first example on the enone synthesis through coupling of"non-functionalized"aldehydes and alkenes as coupling partners,and offers a distinct organocatalytic pathway to the transition metal-catalyzed coupling transformations.

Key words

Enones/Cross dehydrogenative coupling/N-Heterocyclic carbene/Aryl radical/Hydrogen atom transfer

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出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCDCSCD
影响因子:0.771
ISSN:1001-8417
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