Formal Anti-Markovnikov Hydroamination of Terminal Olefins.

ABSTRACT: A new strategy to access linear amines from terminal olefin precursors is reported. This two-step, one-pot hydroamination methodology employs sequential oxidation and reduction catalytic cycles. The formal hydroamination transformation proceeds with excellent regioselectivity, and only the anti-Markovnikov product is observed. Up to 70% yield can be obtained from styrenes or aliphatic olefins and either primary or secondary aromatic amines. Additionally, the scope is broad with respect to the olefin and accommodates a variety of functionalities; we demonstrate that amines with removable aryl protecting groups may be utilized to allow access to a more diverse array of hydroamination adducts.

SUBMITTER: Bronner SM 

PROVIDER: S-EPMC3855355 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature