95127-78-9Relevant articles and documents
Improved solubility and stability of trialkylammonium selenocarboxylate in organic solvents for efficient amidation with azides
Surabhi, Prathima,Wu, Xinghua,Hu, Longqin
, p. 4609 - 4613 (2006)
Trialkylammonium selenocarboxylate, formed in situ from the reaction of diacyl diselenide with piperidine in the presence of diisopropylethylamine, was found to react readily at room temperature with electron-deficient azides to form amides in excellent yields. The trialkylammonium selenocarboxylate salt formed has good solubility and stability in organic solvents. The enhanced stability allowed mild heating to improve the amidation yields with electron-rich azides.
Efficient amidation from carboxylic acids and azides via selenocarboxylates: Application to the coupling of amino acids and peptides with azides
Wu, Xinghua,Hu, Longqin
, p. 765 - 774 (2007/10/03)
(Chemical Equation Presented) A facile one-pot procedure for the coupling of carboxylic acid and azide via selenocarboxylate and selenatriazoline has been developed and successfully applied to the coupling of amino acids and peptides with azides. Selenocarboxylates are readily prepared by the reaction of the activated carboxylic acids with LiAlHSeH under mild conditions. The Selenocarboxylates formed in situ are used to react directly with azides to form the corresponding amides via a selenatriazoline intermediate. Excellent yields were obtained for electron-deficient azides, and moderate to good yields were obtained for electron-rich azides. The selenocarboxylate/azide amidation reaction is clean and chemoselective. It provides an attractive alternative method to the conventional acylation of amines when an amide bond needs to be formed without going through an amine intermediate.
