3826-49-1Relevant academic research and scientific papers
Sulfur–Fluoride Exchange (SuFEx)-Mediated Synthesis of Sterically Hindered and Electron-Deficient Secondary and Tertiary Amides via Acyl Fluoride Intermediates
Smedley, Christopher J.,Barrow, Andrew S.,Spiteri, Christian,Giel, Marie-Claire,Sharma, Pallavi,Moses, John E.
supporting information, p. 9990 - 9995 (2017/08/01)
Amide bond formation is one of the most executed reactions in chemistry and biology. This is largely due to the ubiquity of the amide functional group in biological molecules, natural products and pharmaceutically important drugs. We report here the development of “SuFExAmide”: a new sulfur–fluoride exchange (SuFEx) click chemistry based protocol for the efficient amidation of carboxylic acids via acyl fluoride intermediates. We have developed benzene-1,3-disulfonyl fluoride as a cost effective, powerful and versatile coupling agent, which delivers challenging secondary and tertiary amides in excellent yields from sterically hindered and electron-deficient amines. The straightforward method offers significant benefits over existing protocols in terms of substrate scope, efficiency and ease of operation and is demonstrated by the synthesis of 44 amides, including GNF6702, an antiprotozoal drug candidate. In the majority of cases, the amide products are obtained in high yield without the need for excess reagents or chromatographic purification.
A protocol for amide bond formation with electron deficient amines and sterically hindered substrates
Due-Hansen, Maria E.,Pandey, Sunil K.,Christiansen, Elisabeth,Andersen, Rikke,Hansen, Steffen V. F.,Ulven, Trond
supporting information, p. 430 - 433 (2016/01/12)
A protocol for amide coupling by in situ formation of acyl fluorides and reaction with amines at elevated temperature has been developed and found to be efficient for coupling of sterically hindered substrates and electron deficient amines where standard methods failed.
A convenient, one-pot procedure for the preparation of acyl and sulfonyl fluorides using Cl3CCN, Ph3P, and TBAF(t -BuOH) 4
Kim, Joong-Gon,Jang, Doo Ok
experimental part, p. 3049 - 3052 (2011/02/25)
Various carboxylic acids were converted into acyl fluorides in excellent yields by treatment with trichloroacetonitrile, triphenylphosphine, and TBAF(t-BuOH)4 at room temperature. The reaction was applicable to the preparation of acid-sensitive amino acid fluorides without deprotection or rearrangement
Preparation of acyl fluorides with hydrogen fluoride-pyridine and 1,3-dicyclohexylcarbodiimide
Chen, Chinpiao,Chien, Chin-Tzu,Su, Chu-Hsiang
, p. 75 - 77 (2007/10/03)
This work presents an efficient procedure for preparing acyl fluorides by simply reacting carboxylic acid with hydrogen fluoride-pyridine and 1,3-dicyclohexylcarbodiimide (DCC) in dichloromethane. The acyl fluorides were converted in situ to the corresponding benzyl carboxylic esters by adding benzyl alcohol and triethylamine to the reaction mixture.
