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
Amide Bond Formation Assisted by Vicinal Alkylthio Migration in Enaminones: Metal- and CO-Free Synthesis of α,β-Unsaturated Amides.
Zhuqing Liu,Zhuqing Liu,Fei Huang,Fei Huang,Ping Wu,Ping Wu,Quannan Wang,Quannan Wang,Zhengkun Yu,Zhengkun Yu +9 more
TL;DR: A concise methodology for amide bond (-CONH-) formation assisted by vicinal group migration in alkylthio-functionalized enaminones (α-oxo ketene N, S-acetals) under mild conditions is reported.
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Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis
Karlijn Hollanders,Karlijn Hollanders,Evelien Renders,Charlène Gadais,Charlène Gadais,Dario Masullo,Laurent Van Raemdonck,Clarence Wybon,Charlotte Martin,Wouter A. Herrebout,Bert U. W. Maes,Steven Ballet +11 more
TL;DR: A chemoselective and catalytic transamidation for peptide synthesis is described and amino acid amide/peptidic amide derivatization under Zn catalysis is achieved.
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Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids
TL;DR: The first successful example of the direct synthesis of Weinreb amides using catalytic hydroxy-directed dehydrative amidation of carboxylic acids using the diboronic acid anhydride catalyst is described.
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Metallaphotoredox Decarboxylative Arylation of Natural Amino Acids via an Elusive Mechanistic Pathway
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TL;DR: In this paper , the authors proposed an alternative mechanism for the photoredox-Ni dual-catalyzed decarboxylative arylation of α-amino acids based on control experiments with NiIIArBr complexes, cyclic voltammetry (CV), and computational studies.
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