Allylation, Alkenylation, and Alkynylation of Monofluoromethyl Ketyl Radical Enabled by Photoredox Halogen‐Atom‐Transfer

In this study, we disclose an innovative strategy to access α‐monofluoromethyl secondary alcohol derivatives under mild blue‐light irradiation from brominated fluoroethanol benzoate (BFEB). This reaction takes advantages of bulky silicon radical as a halogen atom transfer (XAT) acceptor to generate...

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Bibliographic Details
Published in:ChemCatChem 2024-12
Main Authors: Sun, Meng‐Qi, Zhai, Shi‐Jing, Nie, Jing, Cheng, Ying, Deng, Xiaojuan, Ding, Guosheng, Cahard, Dominique, Ma, Jun‐An, Zhang, Fa‐Guang
Format: Article
Language:English
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Summary:In this study, we disclose an innovative strategy to access α‐monofluoromethyl secondary alcohol derivatives under mild blue‐light irradiation from brominated fluoroethanol benzoate (BFEB). This reaction takes advantages of bulky silicon radical as a halogen atom transfer (XAT) acceptor to generate the nucleophilic monofluoromethyl ketyl‐type radical, which serves as the key intermediate to couple with a series of phenylsulfonyl‐masked substrates. A broad scope of allyl, alkenyl (Z and E configurations), and alkynyl α‐monofluoromethyl carbinol derivatives were obtained in moderate to good yields.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.202401622