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Electrochemical Vicinal C-H Difunctionalization of Saturated Azaheterocycles.

ABSTRACT: A method to functionalize two vicinal C-H bonds of saturated azaheterocycles is described. The procedure involves subjecting the substrate to a mixture of hydrochloric acid, acetic acid, and acetic anhydride in an undivided electrochemical cell at a constant current, resulting in stereoselective conversion to the corresponding α-acetoxy-β-chloro derivative. The α-position can be readily substituted with a range of other groups, including alkyl, aryl, allyl, alkynyl, alkoxy, or azido functionalities. Furthermore, we demonstrate that the β-chloro position can be engaged in Suzuki cross-coupling. This protocol thus enables the rapid diversification of simple five-, six-, and seven-membered saturated azaheterocycles at two adjacent positions.

SUBMITTER: Kundu G

PROVIDER: S-EPMC10947584 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Electrochemical Vicinal C-H Difunctionalization of Saturated Azaheterocycles.

Kundu Gourab G Lambert Tristan H TH

Journal of the American Chemical Society 20240108 3

A method to functionalize two vicinal C-H bonds of saturated azaheterocycles is described. The procedure involves subjecting the substrate to a mixture of hydrochloric acid, acetic acid, and acetic anhydride in an undivided electrochemical cell at a constant current, resulting in stereoselective conversion to the corresponding α-acetoxy-β-chloro derivative. The α-position can be readily substituted with a range of other groups, including alkyl, aryl, allyl, alkynyl, alkoxy, or azido functionalit ...[more]

PMID: 38190508

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