Copper-catalyzed asymmetric sp3 C-H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Pierre Querard; Inna Perepichka; Eli Zysman-Colman; Chao-Jun Li

doi:10.3762/bjoc.12.260

Copper-catalyzed asymmetric sp³ C-H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Beilstein J Org Chem. 2016 Dec 6:12:2636-2643. doi: 10.3762/bjoc.12.260. eCollection 2016.

Authors

Pierre Querard¹, Inna Perepichka¹, Eli Zysman-Colman², Chao-Jun Li¹

Affiliations

¹ Department of Chemistry, FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
² Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST, UK.

Abstract

This report describes a highly enantioselective oxidative sp³ C-H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)₂(dtbbpy)]PF₆, and chiral copper catalysts provide a mild and highly effective sp³ C-H asymmetric arylation of THIQs.

Keywords: C–H arylation; copper catalyst; enantioselectivity; visible light.