Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins.

ABSTRACT: An efficient method for intermolecular branch-selective allylic C-H amidation has been accomplished via Ir(III) catalysis. The reaction proceeds through initial allylic C-H activation, supported by the isolation and crystallographic characterization of an allyl-Ir(III) intermediate, followed by a subsequent oxidative amidation with readily available dioxazolones as nitrenoid precursors. A diverse range of amides are successfully installed at the branched position of terminal alkenes in good yields and regioselectivities. Importantly, the reaction allows the use of amide-derived nitrenoid precursors avoiding problematic Curtius-type rearrangements.

SUBMITTER: Lei H 

PROVIDER: S-EPMC6986200 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature