首页|Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings
Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings
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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.
EnonesCross dehydrogenative couplingN-Heterocyclic carbeneAryl radicalHydrogen atom transfer
Kun Tang、Fen Su、Shijie Pan、Fengfei Lu、Zhongfu Luo、Fengrui Che、Xingxing Wu、Yonggui Robin Chi
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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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