Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

José A Forni; Nenad Micic; Timothy U Connell; Geethika Weragoda; Anastasios Polyzos

doi:10.1002/anie.202006720

Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

Angew Chem Int Ed Engl. 2020 Oct 12;59(42):18646-18654. doi: 10.1002/anie.202006720. Epub 2020 Aug 18.

Authors

José A Forni¹, Nenad Micic¹, Timothy U Connell², Geethika Weragoda³, Anastasios Polyzos^{1

3}

Affiliations

¹ School of Chemistry, The University of Melbourne, Melbourne, Victoria, 3010, Australia.
² School of Science, RMIT University, Melbourne, Victoria, 3000, Australia.
³ CSIRO Manufacturing, Research Way, Clayton, Victoria, 3168, Australia.

PMID: 32621297
DOI: 10.1002/anie.202006720

Abstract

We report a new visible-light-mediated carbonylative amidation of aryl, heteroaryl, and alkyl halides. A tandem catalytic cycle of [Ir(ppy)₂ (dtb-bpy)]⁺ generates a potent iridium photoreductant through a second catalytic cycle in the presence of DIPEA, which productively engages aryl bromides, iodides, and even chlorides as well as primary, secondary, and tertiary alkyl iodides. The versatile in situ generated catalyst is compatible with aliphatic and aromatic amines, shows high functional-group tolerance, and enables the late-stage amidation of complex natural products.

Keywords: amides; carbonylation; flow chemistry; photoredox catalysis; tandem reactions.

Publication types

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