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Iridium‐Catalyzed Formyl‐Selective Deuteration of Aldehydes
Author(s) -
Kerr William J.,
Reid Marc,
Tuttle Tell
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201702997
Subject(s) - decarbonylation , chemistry , catalysis , iridium , aldehyde , deuterium , combinatorial chemistry , organic chemistry , photochemistry , physics , quantum mechanics
Abstract We report the first direct catalytic method for formyl‐selective deuterium labeling of aromatic aldehydes under mild conditions, using an iridium‐based catalyst designed to favor formyl over aromatic C−H activation. A good range of aromatic aldehydes is selectively labeled, and a one‐pot labeling/olefination method is also described. Computational studies support kinetic product control over competing aromatic labeling and decarbonylation pathways.