Issue 36, 2020

Supported palladium catalyzed aminocarbonylation of aryl iodides employing bench-stable CO and NH3 surrogates

Abstract

A simple, efficient and phosphine free protocol for carbonylative synthesis of primary aromatic amides under polystyrene supported palladium (Pd@PS) nanoparticle (NP) catalyzed conditions has been demonstrated. Herein, instead of using two toxic and difficult to handle gases simultaneously, we have employed the solid, economical, bench stable oxalic acid as the CO source and ammonium carbamate as the NH3 source in a single pot reaction. For the first time, we have applied two non-gaseous surrogates simultaneously under heterogeneous catalyst (Pd@PS) conditions for the synthesis of primary amides using an easy to handle double-vial (DV) system. The developed strategy showed a good functional group tolerance towards a wide range of aryl iodides and afforded primary aromatic amides in good yields. The Pd@PS catalyst was easy to separate and can be recycled up to four consecutive runs with small loss in catalytic activity. We have successfully extended the scope of the methodology to the synthesis of isoindole-1,3-diones from 1,2-dihalobenzene, 2-halobenzoates and 2-halobenzoic acid following double and single carbonylative cyclization approaches.

Graphical abstract: Supported palladium catalyzed aminocarbonylation of aryl iodides employing bench-stable CO and NH3 surrogates

Supplementary files

Article information

Article type
Paper
Submitted
13 Jul 2020
Accepted
27 Aug 2020
First published
28 Aug 2020

Org. Biomol. Chem., 2020,18, 7193-7200

Supported palladium catalyzed aminocarbonylation of aryl iodides employing bench-stable CO and NH3 surrogates

Shaifali, Sheetal, R. Bains, A. Kumar, S. Ram and P. Das, Org. Biomol. Chem., 2020, 18, 7193 DOI: 10.1039/D0OB01445A

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