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

08:00 EDT 12th September 2019 | BioPortfolio

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

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 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 β carbon of an alcohol. Upon β C-H halogenation, aminocyclization, and reductive cleavage, an NH 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.

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This article was published in the following journal.

Name: The Journal of organic chemistry
ISSN: 1520-6904
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