Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl4
Open Access
- 15 September 2017
- journal article
- research article
- Published by Springer Nature in BMC Chemistry
- Vol. 11 (1) , 1-12
Abstract
A general procedure for the synthesis of amides via the direct condensation of carboxylic acids and amines in the presence of TiCl4 is reported. The amidation reaction was performed in pyridine at 85 °C with a wide range of substrates providing the corresponding amide products in moderate to excellent yields and high purity. The reaction proceeds with low yields when both the carboxylic acid and the amine are sterically hindered. The process takes place with nearly complete preservation of the stereochemical integrity of chiral substrates.Keywords
This publication has 40 references indexed in Scilit:
- Macrocyclic Drugs and Synthetic Methodologies toward MacrocyclesMolecules, 2013
- Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH2CF3)3The Journal of Organic Chemistry, 2013
- Titanium(IV) Isopropoxide as an Efficient Catalyst for Direct Amidation of Nonactivated Carboxylic AcidsSynlett, 2012
- The thermal and boron-catalysed direct amide formation reactions: mechanistically understudied yet important processesChemical Communications, 2010
- A preparation of N-Fmoc-N-methyl-α-amino acids and N-nosyl-N-methyl-α-amino acidsAmino Acids, 2008
- N-Methyl-N-nosyl-β3-amino AcidsThe Journal of Organic Chemistry, 2007
- Alternative and Chemoselective Deprotection of the α‐Amino and Carboxy Functions ofN‐Fmoc‐Amino Acid andN‐Fmoc‐Dipeptide Methyl Esters by Modulation of the Molar Ratio in the AlCl3/N,N‐Dimethylaniline Reagent SystemEuropean Journal of Organic Chemistry, 2004
- Highly Stereoselective Conversion of Aryl Peptidyl Ketones into the Corresponding Peptide AlcoholsEuropean Journal of Organic Chemistry, 2004
- 3,4,5-Trifluorobenzeneboronic Acid as an Extremely Active Amidation CatalystThe Journal of Organic Chemistry, 1996
- Carboxamides from Carboxylic Acids by Lewis Acid Catalysis. Use of Principal Properties for Exploring Different Reaction Conditions.Acta Chemica Scandinavica, 1988