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Palladium-Catalyzed Nondirected Late-Stage C-H Deuteration of Arenes.

ABSTRACT: We describe a palladium-catalyzed nondirected late-stage deuteration of arenes. Key aspects include the use of D₂O as a convenient and easily available deuterium source and the discovery of highly active N,N-bidentate ligands containing an N-acylsulfonamide group. The reported protocol enables high degrees of deuterium incorporation via a reversible C-H activation step and features extraordinary functional group tolerance, allowing for the deuteration of complex substrates. This is exemplified by the late-stage isotopic labeling of various pharmaceutically relevant motifs and related scaffolds. We expect that this method, among other applications, will prove useful as a tool in drug development processes and for mechanistic studies.

SUBMITTER: Farizyan M

PROVIDER: S-EPMC8517979 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Nondirected Late-Stage C-H Deuteration of Arenes.

Farizyan Mirxan M Mondal Arup A Mal Sourjya S Deufel Fritz F van Gemmeren Manuel M

Journal of the American Chemical Society 20210928 40

We describe a palladium-catalyzed nondirected late-stage deuteration of arenes. Key aspects include the use of D<sub>2</sub>O as a convenient and easily available deuterium source and the discovery of highly active N,N-bidentate ligands containing an <i>N</i>-acylsulfonamide group. The reported protocol enables high degrees of deuterium incorporation via a reversible C-H activation step and features extraordinary functional group tolerance, allowing for the deuteration of complex substrates. Thi ...[more]

PMID: 34582686

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