Journal Article10.1021/ACS.CHEMREV.6B00237
Nonclassical Routes for Amide Bond Formation
764
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
Native Chemical Ligation and Extended Methods: Mechanisms, Catalysis, Scope, and Limitations
Vangelis Agouridas,Ouafâa El Mahdi,Vincent Diemer,Marine Cargoët,Jean-Christophe Monbaliu,Oleg Melnyk +5 more
TL;DR: The most relevant properties of peptide thioesters, Cys peptides, and common solvents, reagents, additives, and catalysts used for these ligations are presented and the various thiol-based auxiliaries and thiol or selenol amino acid surrogates that have been developed so far are discussed.
487
Homogeneous Catalysis by Cobalt and Manganese Pincer Complexes
Arup Mukherjee,David Milstein +1 more
TL;DR: In this paper, a review of recent progress in the field of homogeneously catalyzed reactions using pincer-type complexes of cobalt and manganese is presented, including acceptorless dehydrogenation, hydrogenation, dehydrogenative coupling, hydrogen borrowing, hydrogen transfer, H-X additions, C-C coupling, alkene polymerization and N2 fixation.
480
The Future of Bioorthogonal Chemistry.
TL;DR: An outlook on the future of bioorthogonal chemistry is presented and currently emerging opportunities and speculate on how bioorthogsonal reactions might be applied in research and translational settings are discussed.
416
Amide Bond Bioisosteres: Strategies, Synthesis, and Successes
TL;DR: The strategic decisions in selecting an amide bioisostere (the why), synthetic routes to each (the how) and success stories of each bioisosterism (the implementation) are reviewed to provide a comprehensive overview of this important toolbox for medicinal chemists.
375
Well-Defined Palladium(II)-NHC Precatalysts for Cross-Coupling Reactions of Amides and Esters by Selective N-C/O-C Cleavage.
TL;DR: The chemistry described here provides a practical approach to functionalize common amide and ester functional groups in organic synthesis and establishes straightforward access to acyl-metal intermediates that enable nonconventional cross-coupling strategies.
342
References
Ionic liquid 1-ethyl-3-methylimidazolium acetate: an attractive solvent for native chemical ligation of peptides
TL;DR: The ionic liquid 1-ethyl-3methylimidazolium acetate ([C2mim][OAc]) was successfully used as alternative solvent for native chemical ligation of peptide fragments to produce model peptide LYRAXCRANK as mentioned in this paper.
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s-Triazene based fluorous coupling reagent for direct amide synthesis
TL;DR: A simple and efficient fluorous coupling reagent TriTFET (2,4, 6-tris-(2,2, 2-trifluoro-ethoxy)-[1,3, 5] triazene) has been designed and synthesized for the direct amidation as mentioned in this paper.
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Aldehyde-Promoted One-Pot Regiospecific Synthesis of Acrylamides Using an in Situ Generated Molybdenum Tetracarbonyl Amine [Mo(CO)4(amine)2] Complex
TL;DR: A novel complex system generated in situ from Mo(CO)6 and an amine is described for the regiospecific aminocarbonylation of various terminal alkynes, making this process palladium-free.
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Reactive Esters in Amide Ligation with β-Hydroxyamines
TL;DR: Amide formation between mildly activated esters and 1,2-amino alcohols without the need for coupling reagents is discussed in this paper, which involves facile intermolecular transesterification and intramolecular ON transacylation.
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In situ protection and deprotection of amines for iron catalyzed oxidative amidation of aldehydes
TL;DR: An environmentally friendly synthetic route by the application of CO2 to synthesize amides via in situ protection and deprotection of amines for iron catalyzed oxidative amidation of aldehydes was developed.
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