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Cooperative Light‐Activated Iodine and Photoredox Catalysis for the Amination of C sp 3 −H Bonds
Author(s) -
Becker Peter,
Duhamel Thomas,
Stein Christopher J.,
Reiher Markus,
Muñiz Kilian
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703611
Subject(s) - amination , photoredox catalysis , photocatalysis , chemistry , catalysis , photochemistry , intramolecular force , iodine , combinatorial chemistry , visible spectrum , organic chemistry , materials science , optoelectronics
An unprecedented method that makes use of the cooperative interplay between molecular iodine and photoredox catalysis has been developed for dual light‐activated intramolecular benzylic C−H amination. Iodine serves as the catalyst for the formation of a new C−N bond by activating a remote Csp3−H bond (1,5‐HAT process) under visible‐light irradiation while the organic photoredox catalyst TPT effects the reoxidation of the molecular iodine catalyst. To explain the compatibility of the two involved photochemical steps, the key N−I bond activation was elucidated by computational methods. The new cooperative catalysis has important implications for the combination of non‐metallic main‐group catalysis with photocatalysis.