Photoredox catalyzed reductive trifluoromethylation of imines a radical umpolung strategy

Visible light-induced radical umpolung chemistry is utilized to synthesize trifluoromethylated unnatural α-amino acid and amine derivatives. This approach utilizes photoredox catalysis to perform a single-electron-transfer reduction of imines generating a N-centred radical that eventually migrates t...

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Published in:Chemical communications (Cambridge, England) England), 2024-11, Vol.6 (89), p.1316-1319
Main Authors: Paul, Hrishikesh, Das, Dibyangshu, Ariyan, S. K, Pradhan, Suman, Chatterjee, Indranil
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Summary:Visible light-induced radical umpolung chemistry is utilized to synthesize trifluoromethylated unnatural α-amino acid and amine derivatives. This approach utilizes photoredox catalysis to perform a single-electron-transfer reduction of imines generating a N-centred radical that eventually migrates to the C-centre followed by a radical-radical cross-coupling to deliver reductive trifluoromethylation products. A photocatalyzed radical-umpolung strategy is developed to synthesize trifluoromethylated α-unnatural amino acids and amines. This method involves the migration of an N-centred radical through an aromatic framework to construct C-CF 3 bond.
ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc03897e