Visible-Light-Induced Photocatalytic C–H Alkylation of Diazo Compounds with Morita–Baylis–Hillman Adducts

Under photocatalytic conditions, diazo compounds undergo proton-coupled electron transfer (PCET) activation, generating highly electrophilic alkyl radicals in situ. These reactive intermediates exhibit marked selectivity toward addition of electron-rich olefins, as consistently demonstrated in previous studies. Notably, in this developed protocol, these radicals undergo addition to the electron-deficient olefin moiety of Morita-Baylis-Hillman (MBH) acetates, followed by acetoxy elimination to afford multifunctionalized olefins. This method demonstrates excellent substrate compatibility, accommodating a wide range of structurally diverse diazoacetate derivatives, and enables efficient transformation of MBH acetates under mild condition.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-10-24
DOI
https://doi.org/10.1021/acs.joc.5c02232
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
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article

Visible-Light-Induced Photocatalytic C–H Alkylation of Diazo Compounds with Morita–Baylis–Hillman Adducts

Dongping Cheng, Xueying Wang, Xiaoliang Xu, Heran Yang et al.
The Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
article

Visible-Light-Induced Photocatalytic C–H Alkylation of Diazo Compounds with Morita–Baylis–Hillman Adducts

Dongping Cheng, Xueying Wang, Xiaoliang Xu, Heran Yang, L. C. LIN
article en

Abstract

Under photocatalytic conditions, diazo compounds undergo proton-coupled electron transfer (PCET) activation, generating highly electrophilic alkyl radicals in situ. These reactive intermediates exhibit marked selectivity toward addition of electron-rich olefins, as consistently demonstrated in previous studies. Notably, in this developed protocol, these radicals undergo addition to the electron-deficient olefin moiety of Morita-Baylis-Hillman (MBH) acetates, followed by acetoxy elimination to afford multifunctionalized olefins. This method demonstrates excellent substrate compatibility, accommodating a wide range of structurally diverse diazoacetate derivatives, and enables efficient transformation of MBH acetates under mild condition.

The Journal of Organic ChemistryVol. 90(44)
Pharmaceutical Biotechnology (Czechia) (CZ), Zhejiang University of Technology (CN)
Openalex Percentile: Top 77%
Cyclopropane Reaction Mechanisms
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