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Reductive Amination by Photoredox Catalysis and Polarity‐Matched Hydrogen Atom Transfer
Author(s) -
Guo Xingwei,
Wenger Oliver S.
Publication year - 2018
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.201711467
Subject(s) - reductive amination , chemistry , photoredox catalysis , iminium , amination , photochemistry , electron transfer , hydrogen atom , ascorbic acid , catalysis , combinatorial chemistry , organic chemistry , photocatalysis , alkyl , food science
The excitation of a Ru II photosensitizer in the presence of ascorbic acid leads to the reduction of iminium ions to electron‐rich α‐aminoalkyl radical intermediates, which are rapidly converted into reductive amination products by thiol‐mediated hydrogen atom transfer (HAT). As a result, the reductive amination of carbonyl compounds with amines by photoredox catalysis proceeds in good to excellent yields and with broad substrate scope and good functional group tolerance. The three key features of this work are 1) the rapid interception of electron‐rich α‐aminoalkyl radical intermediates by polarity‐matched HAT in a photoredox reaction, 2) the method of reductive amination by photoredox catalysis itself, and 3) the application of this new method for temporally and spatially controlled reactions on a solid support, as demonstrated by the attachment of a fluorescent dye on an activated cellulose support by photoredox‐catalyzed reductive amination.