Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp2)-H activation and C(sp3)-H amination

Liangliang Song; Guilong Tian; Johan Van der Eycken; Erik V Van der Eycken

doi:10.3762/bjoc.15.52

Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp²)-H activation and C(sp³)-H amination

Beilstein J Org Chem. 2019 Feb 27:15:571-576. doi: 10.3762/bjoc.15.52. eCollection 2019.

Authors

Liangliang Song¹, Guilong Tian¹, Johan Van der Eycken², Erik V Van der Eycken^{1

3}

Affiliations

¹ Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium.
² Laboratory for Organic and Bio-Organic Synthesis, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 (S.4), B-9000 Ghent, Belgium.
³ Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, Russia.

Abstract

A rhodium(III)-catalyzed intramolecular oxidative annulation of O-substituted N-hydroxyacrylamides for the construction of indolizinones via sequential C(sp²)-H activation and C(sp³)-H amination has been developed. This approach shows excellent functional-group tolerance. The synthesized scaffold forms the core of many natural products with pharmacological relevance.

Keywords: C–H activation; acrylamide; annulation; heterocycles; rhodium.