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A Phosphine-Free Approach to Primary Amides by Palladium-Catalyzed Aminocarbonylation of Aryl and Heteroaryl Iodides Using Methoxylamine Hydrochloride as an Ammonia Equivalent

Sandip T. Gadge, Bhalchandra M. Bhanage*

*Department of Chemistry, Institute of Chemical Technology, N. Parekh Marg, Matunga, Mumbai 400 019, India, Email: bm.bhanageictmumbai.edu.in

S. T. Gadge, B. M. Bhanage, Synlett, 2014, 25, 85-88.

DOI: 10.1055/s-0033-1340162 (free Supporting Information)


Abstract

A palladium-catalyzed aminocarbonylation of aryl and heteroaryl iodides under phosphine-free conditions enables the synthesis of primary amides in excellent yields using methoxylamine hydrochloride as an ammonia equivalent, that undergoes sequential carbonylation and demethoxylation under mild reaction conditions. The procedure does not require a phosphine ligand and takes place in short reaction times at low temperatures.

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Key Words

amides, carbonylation, aminocarbonylation, palladium, catalysis, phosphine-free, cross-coupling


ID: J60-Y2014