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Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

preprint
submitted on 30.04.2020, 07:29 and posted on 30.04.2020, 12:20 by José Augusto Forni, NENAD MICIC, Timothy Connell, GEETHIKA WERAGODA, Anastasios Polyzos

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 via 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 versatility of the in-situ generated catalyst is illustrated by compatibility with aliphatic and aromatic amines, high functional group tolerance and the late-stage amidation of complex natural products.

History

Email Address of Submitting Author

anastasios.polyzos@unimelb.edu.au

Institution

University of Melbourne

Country

Australia

ORCID For Submitting Author

0000-0003-1063-4990

Declaration of Conflict of Interest

No conflicts of interest to declare

Version Notes

Pre-submission version.

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in Angewandte Chemie International Edition

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