4.7 Article

Catalyst-free Decarboxylation and Decarboxylative Giese Additions of Alkyl Carboxylates through Photoactivation of Electron Donor-Acceptor Complex

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 19, Pages 4500-4505

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900803

Keywords

Decarboxylation; Giese Additions; Photoactivation; Redox Active Ester; EDA complex

Funding

  1. National Natural Science Foundation of China (NSFC) [21702039]
  2. Key Research and Development Program of Hainan Province [ZDYF2019155]
  3. Program for Innovative Research Team in University [IRT-16R19]
  4. China Postdoctoral Science Foundation [2018M640588]

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We report herein a catalyst-free method to perform decarboxylative conjugated addition and hydrodecarboxylation of aliphatic N-(acyloxy)phthalimides (redox active esters, RAEs) through photoactivation of electron-donor-acceptor (EDA) complex with Hantzsch ester (HE) in N,N-dimethylacetamide (DMA) solution. The reactions present a green method to decarboxylatively construct carbon-carbon bond and to perform hydrodecarboxylation with broad substrate scope and functional group tolerance under mild blue light irradiation condition without recourse of popularly used photoredox catalysts.

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