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Palladium‐Catalyzed Selective meta ‐C−H Deuteration of Arenes: Reaction Design and Applications
Author(s) -
Bag Sukdev,
Petzold Martin,
Sur Aishanee,
Bhowmick Suman,
Werz Daniel B.,
Maiti Debabrata
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901317
Subject(s) - deuterium , catalysis , palladium , chemistry , phenylacetic acid , selectivity , combinatorial chemistry , acetic acid , organic chemistry , physics , quantum mechanics
Deuterium‐labeled compounds find wide applications in kinetic studies, and within the pharmaceutical industry. An easily removable pyrimidine‐based auxiliary has been employed for the meta ‐C−H deuteration of arenes. The scope of this Pd‐catalyzed deuteration using commercially available [D 1 ]‐ and [D 4 ]‐acetic acid has been demonstrated by its application in phenylacetic acid and phenylmethanesulfonate derivatives. A detailed mechanistic study led us to explore the reversibility of the non‐rate determining C−H activation step. The present study of meta ‐deuterium incorporation illustrates the template morphology in terms of selectivity. The applicability of this method has been demonstrated by the selective deuterium incorporation into various pharmaceuticals.