Regioselective Intermolecular Allylic C-H Amination of Disubstituted Olefins via Rhodium/π-Allyl Intermediates

Jacob S Burman; Simon B Blakey

doi:10.1002/anie.201707021

Regioselective Intermolecular Allylic C-H Amination of Disubstituted Olefins via Rhodium/π-Allyl Intermediates

Angew Chem Int Ed Engl. 2017 Oct 23;56(44):13666-13669. doi: 10.1002/anie.201707021. Epub 2017 Oct 4.

Authors

Jacob S Burman¹, Simon B Blakey¹

Affiliation

¹ Department of Chemistry, Emory University, 1515 Dickie Dr., Atlanta, GA, 30322, USA.

PMID: 28913956
DOI: 10.1002/anie.201707021

Abstract

A method for catalytic intermolecular allylic C-H amination of trans-disubstituted olefins is reported. The reaction is efficient for a range of common nitrogen nucleophiles bearing one electron-withdrawing group, and proceeds under mild reaction conditions. Good levels of regioselectivity are observed for a wide range of electronically diverse trans-β-alkyl styrene substrates.

Keywords: allylic compounds; amination; reaction mechanisms; regioselectivity; rhodium.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.