Mechanism of Iminium Salt-Catalyzed C(sp³)-H Amination: Factors Controlling Hydride Transfer versus H-Atom Abstraction.

ABSTRACT: Carbon-nitrogen bonds are extremely prevalent in pharmaceuticals, natural products, and other biologically relevant molecules such as nucleic acids and proteins. Intermolecular amination of C(sp³)-H bonds by catalytic nitrene transfer is a promising method for forging C-N bonds. An organocatalytic approach to nitrene transfer by way of an iminium salt offers a site-selective method for C(sp³)-H amination. Understanding of this amination mechanism including the nature of the relevant intermediates and the factors controlling the mechanism of the N-H bond formation step would aid in the design of catalysts and C(sp³)-H amination methods. In this work, the mechanism of the iminium salt-catalyzed C(sp³)-H amination via nitrene transfer was elucidated

SUBMITTER: Rotella ME 

PROVIDER: S-EPMC8188841 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature