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Copper-Catalyzed 1,2-Aminocyanation of Unactivated Alkenes via Cyano Migration.

ABSTRACT: A copper-catalyzed aminocyanation of alkenes has been achieved through distal cyano migration using O-benzoylhydroxylamines and N-fluorobenzenesulfonimides. This method offers a rapid approach to generate diverse ?-amino and ?-sulfonimido nitriles. These reactions feature mild conditions, tolerance of sensitive functional groups, and excellent regioselectivity. Mechanistic studies suggest that these transformations are initiated by a copper-catalyzed amination step followed by a cyano migration step.

SUBMITTER: Kwon Y

PROVIDER: S-EPMC7505134 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Copper-Catalyzed 1,2-Aminocyanation of Unactivated Alkenes via Cyano Migration.

Kwon Yungeun Y Wang Qiu Q

Organic letters 20200508 11

A copper-catalyzed aminocyanation of alkenes has been achieved through distal cyano migration using <i>O</i>-benzoylhydroxylamines and <i>N</i>-fluorobenzenesulfonimides. This method offers a rapid approach to generate diverse β-amino and β-sulfonimido nitriles. These reactions feature mild conditions, tolerance of sensitive functional groups, and excellent regioselectivity. Mechanistic studies suggest that these transformations are initiated by a copper-catalyzed amination step followed by a cy ...[more]

PMID: 32383382

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