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.
Authors
- Dongping Cheng (ORCID: https://orcid.org/0000-0001-6354-1726)
- Xueying Wang (ORCID: https://orcid.org/0009-0005-5908-6659)
- Xiaoliang Xu (ORCID: https://orcid.org/0000-0002-1192-3156)
- Heran Yang (ORCID: https://orcid.org/0000-0002-3430-4761)
- L. C. LIN
Institutions
- Pharmaceutical Biotechnology (Czechia) (CZ)
- Zhejiang University of Technology (CN)
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
- 0.00