Synthesis and Application of Amino‐1H‐1,2,3‐triazolium Salts

A fluoride-mediated nucleophilic aromatic amination of chloro-1H-1,2,3-triazolium salts was reported. The reaction proceeds under an air atmosphere and benefits from a broad scope and a high functional group tolerance. The deprotonation of amino-1H-1,2,3-triazolium salts provided triazolium-based N-heterocyclic imines, which exhibited high catalytic activity for the cyanosilylation of ketones.

Abstract

Herein, we developed a fluoride-mediated nucleophilic aromatic amination of chloro-1H-1,2,3-triazolium salts. Various functional groups were tolerated in this reaction, which enabled the synthesis of functionalized amino-1H-1,2,3-triazolium salts. In addition, we investigated the catalytic properties of triazolium-based N-heterocyclic imines (NHIs) for cyanosilylation of ketones. The substituent was found to play a crucial role for inducing high catalytic activity.

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