Tetrahedron

2-Substituted-3-acylindoles through the palladium-catalysed carbonylative cyclization of 2-alkynyltrifluoroacetanilides with aryl halides and vinyl triflates

A Arcadi, S Cacchi, V Carnicelli, F Marinelli

Index: Arcadi; Cacchi; Carnicelli; Marinelli Tetrahedron, 1994 , vol. 50, # 2 p. 437 - 452

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Citation Number: 122

Abstract

The palladium-catalysed reaction of readily accessible 2-alkynyltrifluoroacetanilides with aryl hanides and vinyl triflates under a carbon monoxide atmosphere (1 or 7 atm) the presence of potassium carbonate produce s 2-substituted-3-acyl indoles in fair to good yield. The acidity of the nitrogen-hydrogen bond proved to be of primary importance for the success of the reaction. The methodology has been applied to the synthesis of ...