Development of an Imine Chaperone for Selective C-H Functionalization of Alcohols via Radical Relay.

ABSTRACT: The design of a radical relay chaperone to promote selective C-H functionalizations is described. A saccharin-based imine was found to be uniquely suited to effect C-H amination of alcohols via an in situ generated hemiaminal. This radical chaperone facilitates the mild generation of an N-centered radical while also directing its regioselective H atom transfer (HAT) to the ? carbon of an alcohol. Upon ? C-H halogenation, aminocyclization, and reductive cleavage, an NH2 is formally added vicinal to an alcohol. The development, synthetic utility, and chemo-, regio-, and stereoselectivity of this imine chaperone-mediated C-H amination is presented herein.

SUBMITTER: Nakafuku KM 

PROVIDER: S-EPMC6948922 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature