A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system

@article{RouhiSaadabad2015AOF,
  title={A One-Pot, fast, and efficient amidation of carboxylic acids, $\alpha$-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system},
  author={Hamed Rouhi-Saadabad and Batool Akhlaghinia},
  journal={Phosphorus, Sulfur, and Silicon and the Related Elements},
  year={2015},
  volume={190},
  pages={1703 - 1714}
}
GRAPHICAL ABSTRACT Abstract Triphenylphosphine (PPh3)/N-chlorobenzotriazole (NCBT), and amine (primary and secondary aliphatic amines and also substituted anilines) in CH2Cl2 efficiently converted carboxylic acids, α-amino acids, and sulfonic acids to the corresponding amides and sulfonamides at room temperature. Good to excellent yields, inexpensive, and fast reaction conditions are the important features of this procedure. 
3 Citations
Amide Synthesis through the In Situ Generation of Chloro- and Imido-Phosphonium Salts
TLDR
A methodology for the amidation of carboxylic acids by generating phosphonium salts in situ from N-chlorophthalimide and triphenylphosphine is described and an acyloxy-phosphonium species is generated.
Recent advances in the synthesis of organic chloramines and their insights into health care
Organic nitrogen–chlorine compounds and their derivatives are important heterocyclic motifs, exhibiting applications such as N-chlorinating agents, analytical reagents, disinfectants, antipathogens,

References

SHOWING 1-10 OF 80 REFERENCES
A simple and regioselective one-pot procedure for the direct N-acylation of some purine and pyrimidine nucleobases via carboxylic acids using cyanuric chloride
A facile and selective one-pot N-acylation of nucleobases via carboxylic acids using cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) is described. In this protocol, the reaction of diverse
A Facile One-Pot Transformation of Carboxylic Acids to Amides
Abstract Carboxylic acids, converted in situ into carboxylic-(p-nitrobenzene)sulfonic anhydrides using p-nitrobenzenesulfonyl chloride, Et3N, and DMAP in CH3CN, react with primary or secondary
An Efficient Protocol for the Amidation of Carboxylic Acids Promoted by Trimethyl Phosphite and Iodine
A practical, one-pot protocol is described for the conversion of carboxylic acids into amides through carboxyl activation by the reagent combination of trimethyl phosphite and iodine. This method
Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH2CF3)3
TLDR
B(OCH2CF3)3, prepared from readily available B2O3 and 2,2,2-trifluoroethanol, is as an effective reagent for the direct amidation of a variety of carboxylic acids with a broad range of amines, via transamidation of dimethylformamide.
A Facile Synthesis of Carboxamides by Dehydration Condensation Between Free Carboxylic Acids and Amines Using O,O'-Di(2-pyridyl) Thiocarbonate as a Coupling Reagent
Carboxamides are prepared in high yields by dehydration condensation between nearly equimolar amounts of free carboxylic acids and amines both of which involve secondary or tertiary alkyl substituted
Direct and Facile Synthesis of Acyl Isothiocyanates from Carboxylic Acids Using Trichloroisocyanuric Acid/Triphenylphosphine System
A mild, efficient, and practical method for one-step synthesis of alkanoyl and aroyl isothiocyanates from carboxylic acids using a safe and inexpensive mixed reagent, trichloroisocyanuric
A convenient method for the synthesis of carboxamides and thioesters by using tetrakis (2-methylimidazol-1-yl)silane
Tetrakis(2-methylimidazol-l-yl)silane [Si(2-Me-Im) 4 ], a new dehydrating reagent having silicon-imidazole linkage, reacted readily with carboxylic acids at room temperature to form the corresponding
One-pot synthesis of amides from aldehydes and amines via C-H bond activation.
TLDR
A one-pot synthesis of amides from aldheydes with N-chloroamines, prepared in situ from amines, has been developed and appears simple and convenient, has a wide substrate scope and makes use of cheap, abundant, and easily available reagents.
Borate esters as convenient reagents for direct amidation of carboxylic acids and transamidation of primary amides.
TLDR
Simple borates serve as effective promoters for amide bond formation with a variety of carboxylic acids and amines and can be used for the straightforward conversion of primary amides to secondary amides via transamidation.
...
1
2
3
4
5
...