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Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki-Miyaura-Coupling and Transfer-Hydrogenation Cascade.

ABSTRACT: We report a means to achieve the addition of two disparate nucleophiles to the amide carbonyl carbon in a single operational step. Our method takes advantage of non-precious-metal catalysis and allows for the facile conversion of amides to chiral alcohols via a one-pot Suzuki-Miyaura cross-coupling/transfer-hydrogenation process. This study is anticipated to promote the development of new transformations that allow for the conversion of carboxylic acid derivatives to functional groups bearing stereogenic centers via cascade processes.

SUBMITTER: Boit TB

PROVIDER: S-EPMC7855255 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki-Miyaura-Coupling and Transfer-Hydrogenation Cascade.

Boit Timothy B TB Mehta Milauni M MM Kim Junyong J Baker Emma L EL Garg Neil K NK

Angewandte Chemie (International ed. in English) 20201130 5

We report a means to achieve the addition of two disparate nucleophiles to the amide carbonyl carbon in a single operational step. Our method takes advantage of non-precious-metal catalysis and allows for the facile conversion of amides to chiral alcohols via a one-pot Suzuki-Miyaura cross-coupling/transfer-hydrogenation process. This study is anticipated to promote the development of new transformations that allow for the conversion of carboxylic acid derivatives to functional groups bearing st ...[more]

PMID: 33029868

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Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic Amides.

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