Palladium-Catalyzed Selective meta-C-H Deuteration of Arenes: Reaction Design and Applications
Sukdev Bag1, Martin Petzold2, Aishanee Sur1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, 400076, Mumbai, India.
Abstract:
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 [D1 ]- and [D4 ]-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.
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