An Experimental and Computational Assessment of Acid-Catalyzed Azide-Nitrile Cycloadditions

D Cantillo, B Gutmann, CO Kappe

Index: Cantillo, David; Gutmann, Bernhard; Kappe, C. Oliver Journal of Organic Chemistry, 2012 , vol. 77, # 23 p. 10882 - 10890

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Citation Number: 17

Abstract

The mechanism of the azide–nitrile cycloaddition mediated by different Brønsted and Lewis acids has been addressed through DFT calculations. In all cases activation of the nitrile substrate by the Brønsted or Lewis acid catalyst was found to be responsible for the rate enhancement. According to DFT calculations the cycloaddition proceeds in a stepwise fashion involving the initial formation of an open-chain imidoyl azide intermediate. Kinetic ...