Journal Article10.1021/ACS.CHEMREV.6B00237
Nonclassical Routes for Amide Bond Formation
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TL;DR: The present review offers an overview of nonclassical (e.g., with no pre- or in situ activation of a carboxylic acid partner) approaches for the construction of amide bonds.
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Abstract: The present review offers an overview of nonclassical (e.g., with no pre- or in situ activation of a carboxylic acid partner) approaches for the construction of amide bonds. The review aims to comprehensively discuss relevant work, which was mainly done in the field in the last 20 years. Organization of the data follows a subdivision according to substrate classes: catalytic direct formation of amides from carboxylic and amines (section 2); the use of carboxylic acid surrogates (section 3); and the use of amine surrogates (section 4). The ligation strategies (NCL, Staudinger, KAHA, KATs, etc.) that could involve both carboxylic acid and amine surrogates are treated separately in section 5.
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Citations
NDTP Mediated Direct Rapid Amide and Peptide Synthesis without Epimerization.
Yiping Li,Jingyue Li,Guangjun Bao,Chan Yong Yu,Yuyang Liu,Zeyuan He,Peng Wang,Wen-Jing Ma,Junqiu Xie,Wang-Jie Sun,Rui Wang +10 more
TL;DR: An unprecedented mild, nonirritating, conveniently available, and recyclable coupling reagent NDTP was explored, which could activate the carboxylic acids via acyl thiocyanide and enable the rapid amide and peptide synthesis at very mild conditions.
28
Intramolecular Transamidation of Secondary Amides via Visible-Light-Induced Tandem Reaction.
TL;DR: In this tandem reaction, the Rose Bengal-catalyzed photo-oxidative coupling of arylglycine esters and enamides generates N-acylimines, which undergo intramolecular transamidation and imine hydrolysis to afford bioactive acyl Mannich base derivatives under metal-free and mild conditions.
28
Minimizing HCN in DIC/Oxyma-Mediated Amide Bond-Forming Reactions
Marion Erny,Marika Lundqvist,Jon H. Rasmussen,Olivier Ludemann-Hombourger,Frédéric Bihel,Jan Pawlas +5 more
TL;DR: Aiming at advancing protocols for safer, environmentally sensible peptide synthesis, findings with regard to the occurrence of hydrogen cyanide (HCN, prussic acid) in amide bond-formin are reported.
27
Near-Ambient-Temperature Dehydrogenative Synthesis of the Amide Bond: Mechanistic Insight and Applications.
TL;DR: In this paper, a system for amide bond synthesis via acceptorless dehydrogenative coupling of amines and alcohols using ruthenium PNNH complexes is presented.
27
Chemoselective Transamidation of Thioamides by Transition-Metal-Free N-C(S) Transacylation.
TL;DR: The first general method for the direct transamidation of thioamides by highly chemoselective N-C(S) transacylation is reported, enabling to rationally manipulate nucleophilic addition to the thioamide bond.
27
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