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Radical‐Based C−C Bond‐Forming Processes Enabled by the Photoexcitation of 4‐Alkyl‐1,4‐dihydropyridines
Author(s) -
Buzzetti Luca,
Prieto Alexis,
Roy Sudipta Raha,
Melchiorre Paolo
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709571
Subject(s) - photoexcitation , photochemistry , chemistry , homolysis , alkyl , radical , bond cleavage , reagent , electron transfer , reactivity (psychology) , excited state , photocatalysis , catalysis , organic chemistry , medicine , physics , alternative medicine , pathology , nuclear physics
We report herein that 4‐alkyl‐1,4‐dihydropyridines (alkyl‐DHPs) can directly reach an electronically excited state upon light absorption and trigger the generation of C(sp 3 )‐centered radicals without the need for an external photocatalyst. Selective excitation with a violet‐light‐emitting diode turns alkyl‐DHPs into strong reducing agents that can activate reagents through single‐electron transfer manifolds while undergoing homolytic cleavage to generate radicals. We used this photochemical dual‐reactivity profile to trigger radical‐based carbon–carbon bond‐forming processes, including nickel‐catalyzed cross‐coupling reactions.