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Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides
Author(s) -
Forni José A.,
Micic Nenad,
Connell Timothy U.,
Weragoda Geethika,
Polyzos Anastasios
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202006720
Subject(s) - aryl , alkyl , catalysis , chemistry , iridium , halide , tandem , catalytic cycle , carbonylation , photoredox catalysis , combinatorial chemistry , primary (astronomy) , functional group , organic chemistry , photocatalysis , carbon monoxide , materials science , physics , polymer , astronomy , composite material
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.