2013
DOI: 10.1021/ol4002625
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l-Proline: An Efficient Catalyst for Transamidation of Carboxamides with Amines

Abstract: In the presence of a catalytic amount of L-proline (10 mol %), transamidations of carboxamides with amines were achieved under solvent-free conditions. The transamidation process is compatible with a wide range of amines.

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Cited by 158 publications
(54 citation statements)
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“…Since this report, a number of alternative catalysts and reagents for transamidation reactions have been reported including hydroxylamine hydrochloride, 31 Cp 2 ZrCl 2 , 32 Cu(OAc) 2 , 33 PhI(OAc) 2 , 34 boric acid, 35 CeO 2 36 and l -proline. 37 In many cases these reagents are cheap and readily available, and the reactions have a wide substrate scope. On this basis, it therefore seemed that the potential application of B(OCH 2 CF 3 ) 3 as a reagent for transamidation of primary amides is somewhat limited.…”
Section: Resultsmentioning
confidence: 99%
“…Since this report, a number of alternative catalysts and reagents for transamidation reactions have been reported including hydroxylamine hydrochloride, 31 Cp 2 ZrCl 2 , 32 Cu(OAc) 2 , 33 PhI(OAc) 2 , 34 boric acid, 35 CeO 2 36 and l -proline. 37 In many cases these reagents are cheap and readily available, and the reactions have a wide substrate scope. On this basis, it therefore seemed that the potential application of B(OCH 2 CF 3 ) 3 as a reagent for transamidation of primary amides is somewhat limited.…”
Section: Resultsmentioning
confidence: 99%
“…Based on experimental observations and literature reports of similar reaction [28][29][30], a plausible reaction mechanism was proposed for proline-based ILs catalyzed …”
Section: Resultsmentioning
confidence: 99%
“…In view of the above perceptions, the development of benign and metal-free transamidation procedures with high yield and selectivity is desirable. In continuation of our interest on the development of environmentfriendly transamidation catalysts [35][36][37][38][39], we wish to report a general L-proline-catalysed transthioamidation of primary amides with amines under solvent-free conditions [40]. To the best of our knowledge very rare reports available for the efficient transthioamidations under neat conditions [41].…”
Section: Introductionmentioning
confidence: 99%