Citation: Kun Tang, Fen Su, Shijie Pan, Fengfei Lu, Zhongfu Luo, Fengrui Che, Xingxing Wu, Yonggui Robin Chi. Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings[J]. Chinese Chemical Letters, ;2024, 35(9): 109495. doi: 10.1016/j.cclet.2024.109495 shu

Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings

Kun Tang ^{a, 1} ,
Fen Su ^{a, 1} ,
Shijie Pan ^a ,
Fengfei Lu ^a ,
Zhongfu Luo ^a ,
Fengrui Che ^a ,
Xingxing Wu ^{a, *,} ,
Yonggui Robin Chi ^{a, b, **,}

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

^**

wuxx@gzu.edu.cn

robinchi@ntu.edu.sg

Received Date: 23 October 2023
Revised Date: 22 December 2023
Accepted Date: 2 January 2024
Available Online: 12 January 2024

Figures(3)

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 particular 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.
- Enones,
- Cross dehydrogenative coupling,
- N-Heterocyclic carbene,
- Aryl radical,
- Hydrogen atom transfer
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