scholarly journals Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles

2015 ◽  
Vol 11 ◽  
pp. 2158-2165 ◽  
Author(s):  
Wen Ding ◽  
Shaoyu Mai ◽  
Qiuling Song
Keyword(s):  
Molecular Oxygen ◽  
Carboxylic Acids ◽  
Essential Role ◽  
Mechanistic Studies ◽  
Direct Formation ◽  
Direct Amidation

A copper-catalyzed oxidative direct formation of amides from nonactivated carboxylic acids and azoles with dioxygen as an activating reagent is reported. The azole amides were produced in good to excellent yields with a broad substrate scope. The mechanistic studies reveal that oxygen plays an essential role in the success of the amidation reactions with copper peroxycarboxylate as the key intermediate. Transamidation occurs smoothly between azole amide and a variety of amines.

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. 

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.

ChemInform Abstract: Oxidation of Aldehydes into Carboxylic Acids with Molecular Oxygen Using Nickel(II) Complex Catalyst.

ChemInform ◽  
2010 ◽  
Vol 23 (44) ◽  
pp. no-no ◽  
Author(s):  
T. YAMADA ◽  
O. RHODE ◽  
T. TAKAI ◽  
T. MUKAIYAMA
Keyword(s):  
Molecular Oxygen ◽  
Carboxylic Acids ◽  
Complex Catalyst

scholarly journals Copper mediated decarboxylative direct C–H arylation of heteroarenes with benzoic acids

2016 ◽  
Vol 52 (7) ◽  
pp. 1432-1435 ◽  
Author(s):  
Tuhin Patra ◽  
Sudip Nandi ◽  
Santosh K. Sahoo ◽  
Debabrata Maiti
Keyword(s):  
Molecular Oxygen ◽  
Carboxylic Acids ◽  
Dual Role ◽  
Benzoic Acids

Copper mediated decarboxylative direct C–H arylation of 5-membered heteroarenes with aryl carboxylic acids is developed using the molecular oxygen as sole oxidant. Copper plays the dual role in decarboxylation and C–H arylation.

scholarly journals Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Zhan Li ◽  
Ke-Feng Wang ◽  
Xin Zhao ◽  
Huihui Ti ◽  
Xu-Ge Liu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Late Stage ◽  
Materials Science ◽  
Reaction Pathway ◽  
Chemical Conversion ◽  
Primary Amines ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Aliphatic Acids ◽  
Redox Active

Abstract Alkyl carboxylic acids as well as primary amines are ubiquitous in all facets of biological science, pharmaceutical science, chemical science and materials science. By chemical conversion to redox-active esters (RAE) and Katritzky’s N-alkylpyridinium salts, respectively, alkyl carboxylic acids and primary amines serve as ideal starting materials to forge new connections. In this work, a Mn-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines is disclosed. A series of C-X (X = S, Se, Te, H, P) and C-C bonds are efficiently constructed under simple and mild reaction conditions. The protocol is applicable to the late-stage modification of some structurally complex natural products or drugs. Preliminary mechanistic studies suggest the involvement of radicals in the reaction pathway.

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).

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