Direct Palladium-Catalyzed β-Arylation of Lactams

Ming Chen; Feipeng Liu; Guangbin Dong

doi:10.1002/anie.201800958

Direct Palladium-Catalyzed β-Arylation of Lactams

Angew Chem Int Ed Engl. 2018 Mar 26;57(14):3815-3819. doi: 10.1002/anie.201800958. Epub 2018 Mar 5.

Authors

Ming Chen¹, Feipeng Liu^{1

2}, Guangbin Dong¹

Affiliations

¹ Department of Chemistry, University of Chicago, Chicago, IL 60637, USA.
² Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, China.

PMID: 29424015
DOI: 10.1002/anie.201800958

Abstract

A direct and catalytic method is reported here for β-arylation of N-protected lactams with simple aryl iodides. The transformation is enabled by merging soft enolization of lactams, palladium-catalyzed desaturation, Ar-X bond activation, and aryl conjugate addition. The reaction is operated under mild reaction conditions, is scalable, and is chemoselective. Application of this method to concise syntheses of pharmaceutically relevant compounds is demonstrated.

Keywords: C−H activation; heterocylces; lactams; palladium; reaction mechanisms.

Publication types

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