Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines.

ABSTRACT: The intermolecular hydroamination of unactivated alkenes with simple dialkyl amines remains an unsolved problem in organic synthesis. We report a catalytic protocol for efficient additions of cyclic and acyclic secondary alkyl amines to a wide range of alkyl olefins with complete anti-Markovnikov regioselectivity. In this process, carbon-nitrogen bond formation proceeds through a key aminium radical cation intermediate that is generated via electron transfer between an excited-state iridium photocatalyst and an amine substrate. These reactions are redox-neutral and completely atom-economical, exhibit broad functional group tolerance, and occur readily at room temperature under visible light irradiation. Certain tertiary amine products generated through this method are formally endergonic r

SUBMITTER: Musacchio AJ 

PROVIDER: S-EPMC5426363 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature