scholarly journals Silicon compounds as stoichiometric coupling reagents for direct amidation

2021 ◽  
Author(s):  
Joshua J. Davies ◽  
D. Christopher Braddock ◽  
Paul D. Lickiss
Keyword(s):  
Carboxylic Acids ◽  
Coupling Reagents ◽  
Silicon Compounds ◽  
Direct Amidation

This review covers all the reported use of stoichiometric silicon reagents for direct amidation of carboxylic acids with amines, commencing with the first example in 1969 up until April 2021. 

scholarly journals Site-specific Umpolung amidation of carboxylic acids via triplet synergistic catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yunyun Ning ◽  
Shuaishuai Wang ◽  
Muzi Li ◽  
Jie Han ◽  
Chengjian Zhu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Amide Bond ◽  
Coupling Reagents ◽  
Complex Molecules ◽  
Bond Forming ◽  
Synergistic Catalysis ◽  
Wide Range ◽  
Amidation Reaction ◽  
Forming Methods

AbstractDevelopment of catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. In this paper, we disclose an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by the triplet synergistic catalysis of FeI2, P(V)/P(III) and photoredox catalysis, which avoids the production of byproducts from stoichiometric coupling reagents. A wide range of carboxylic acids, including aliphatic, aromatic and alkenyl acids participate smoothly in such reactions, generating structurally diverse amides in good yields (86 examples, up to 97% yield). This Umpolung amidation strategy opens a method to address challenging regioselectivity issues between nucleophilic functional groups, and complements the functional group compatibility of the classical amidation protocols. The synthetic robustness of the reaction is demonstrated by late-stage modification of complex molecules and gram-scale applications.

Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support

2015 ◽  
Vol 17 (5) ◽  
pp. 3157-3163 ◽  
Author(s):  
Andrea Ojeda-Porras ◽  
Alejandra Hernández-Santana ◽  
Diego Gamba-Sánchez
Keyword(s):  
Fatty Acids ◽  
Microwave Irradiation ◽  
Carboxylic Acids ◽  
Silica Gel ◽  
Solid Support ◽  
Secondary Amines ◽  
Primary And Secondary Amines ◽  
Direct Amidation

A highly improved methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. Several examples using aliphatic, aromatic, unsaturated and fatty acids combined with primary and secondary amines are shown.

Pyrrolidide formation as a side reaction during activation of carboxylic acids by phosphonium salt coupling reagents

1999 ◽  
Vol 6 (4) ◽  
pp. 243-245 ◽  
Author(s):  
Jordi Alsina ◽  
George Barany ◽  
Fernando Albericio ◽  
Steven A. Kates
Keyword(s):  
Carboxylic Acids ◽  
Phosphonium Salt ◽  
Side Reaction ◽  
Coupling Reagents

A multigram-scale lower E-factor procedure for MIBA-catalyzed direct amidation and its application to the coupling of alpha and beta aminoacids

2015 ◽  
Vol 17 (7) ◽  
pp. 4016-4028 ◽  
Author(s):  
Solmaz Fatemi ◽  
Nicolas Gernigon ◽  
Dennis G. Hall
Keyword(s):  
Amino Acids ◽  
Carboxylic Acids ◽  
Direct Amidation

More economical conditions for direct amidation between amines and carboxylic acids, including α- and β-amino acids, have been optimized using the MIBA catalyst (5-methoxy-2-iodophenylboronic acid, 6).

ChemInform Abstract: Direct Amidation of Carboxylic Acids with Tertiary Amines: Amide Formation over Copper Catalysts Through C-N Bond Cleavage.

ChemInform ◽  
2015 ◽  
Vol 46 (8) ◽  
pp. no-no
Author(s):  
Biquan Xiong ◽  
Longzhi Zhu ◽  
Xiaofeng Feng ◽  
Jian Lei ◽  
Tieqiao Chen ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Bond Cleavage ◽  
Copper Catalysts ◽  
Tertiary Amines ◽  
Amide Formation ◽  
Direct Amidation

Repurposing n-butyl stannoic acid as highly efficient catalyst for direct amidation of carboxylic acids with amines

2018 ◽  
Vol 59 (52) ◽  
pp. 4582-4586 ◽  
Author(s):  
Santoshkumar M. Potadar ◽  
Anil S. Mali ◽  
Krishnakant T. Waghmode ◽  
Ganesh U. Chaturbhuj
Keyword(s):  
Carboxylic Acids ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
Direct Amidation
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