An Environmentally Benign, Catalyst‐Free N−C Bond Cleavage/Formation of Primary, Secondary, and Tertiary Unactivated Amides. Issue 41 (4th November 2021)

• Record Type: Journal Article
• Authors: Kumar, Vishal; Dhawan, Sanjeev; Girase, Pankaj Sanjay; Singh, Parvesh; Karpoormath, Rajshekhar
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 41(2022)
• Page Start: 5627
• Page End: 5639
• Publication Date: 2021-11-04
• Subjects: Amine -- Amide -- Hydrochloride salt -- Metal-free chemistry -- Transamidation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202101114
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Herein, we report an operationally simple, cheap, and catalyst‐free method for the transamidation of a diverse range of unactivated amides furnishing the desired products in excellent yields. This protocol is environmentally friendly and operates under extremely mild conditions without using any promoter or additives. Significantly, this strategy has been implied in the chemoselective synthesis of a pharmaceutical molecule, paracetamol, on a gram‐scale with excellent yield. We anticipate that this universally applicable strategy will be of great interest in drug discovery, biochemistry, and organic synthesis. Abstract : An unprecedented methodology for the synthesis of a variety of organic amides through the coupling of wide range of unactivated primary, secondary, and tertiary diversified amides, with different amines is reported. The acid‐promoted reaction is proposed to proceed through carbonyl activation and is accompanied by broad substrate scope with high tolerance for functional groups.