n-Bu₄NI/TBHP-catalyzed C–N bond formation via cross-dehydrogenative coupling of 1H-1,2,4-triazoles (N–H) and methylarenes (C_sp3–H)

Abstract

An efficient n-Bu4NI/TBHP-catalyzed protocol for C–N bond formation via cross-dehydrogenative coupling of 1H-1,2,4-triazoles (N–H) and methylarenes (Csp3–H) has been developed under metal free conditions.

A Study On Synthesis, Biological Activities and Molecular Modelling of Some Novel Trisubstituted 1,2,4‐Triazole Derivatives

“…In a study by Kuang et al ., 1‐(4‐fluorobenzyl)‐3,5‐diphenyl‐ 1H ‐1,2,4‐triazole was synthesized from the cyclization reaction of one molecule of 4‐fluorobenzylamine and two molecules of benzonitrile in the presence of Cu(OAC) 2 ‐catalyst . In another study, N ‐substituted benzyl‐1,2,4‐triazoles were obtained from dehydrogenative coupling reactions with 1,2,4‐triazoles and methylenes in the presence of n‐Bu 4 NI /TBHP‐catalyst, by Abebe and colleagues . In this work, we synthesized in higher yields of N‐benzyl‐1,2,4‐triazoles ( 2 a‐e ) from the reaction of the 3,5‐diphenyl‐ 1H ‐1,2,4‐triazole and substituted benzyl bromides in ethanolic sodium ethoxide.…”

“…[39] In another study, N-substituted benzyl-1,2,4-triazoles were obtained from dehydrogenative coupling reactions with 1,2,4-triazoles and methylenes in the presence of n-Bu 4 NI /TBHP-catalyst, by Abebe and colleagues. [40] In this work, we synthesized in higher yields of N-benzyl-1,2,4-triazoles (2 a-e) from the reaction of the 3,5-diphenyl-1H-1,2,4-triazole and substituted benzyl bromides in ethanolic sodium ethoxide. Although the ethyl (3,5-diphenyl-1H-1,2,4-triazole-1-yl)acetate (3) was known, [41] the synthesis method of it was not given in the literature.…”

An Efficient N -Bu4 NI-Catalyzed Protocol for the Synthesis of Hemiaminal Ethers by Linking Ethers with 1,2,4-Triazoles and Indazoles via Cross Dehydrogenative Coupling Reaction

“…However, n ‐Bu 4 NI catalyzed formation of hemiaminal ethers via sp 3 C−H activation is rarely exploited, especially for 1 H ‐1,2,4‐triazoles and 1 H ‐indazoles. Very recently, we have reported a direct benzylation of 1 H ‐1,2,4‐triazoles with active benzyl C−H substrates via metal‐free CDC reaction, and some selected cyclic ethers were also found to be compatible with this protocol . On basis of this, herein, we wish to describe a method for the synthesis of hemiaminal ethers by combining various ethers with 1 H ‐1,2,4‐triazoles and 1 H‐ indazoles under metal‐free conditions in detail.…”

Recent Progress in the Construction of C−N Bonds via Metal‐Free Radical C(sp3)−H Functionalization

“…In 2016, an elegant protocol for C−N bond formation via cross‐dehydrogenative coupling of 1 H ‐1,2,4‐triazoles with methylarenes under the ( n‐ Bu) 4 NI/TBHP system was reported by the Vidavalur group (Scheme ) . The transformation does not need anyr solvent, while the addition of a solvent reduced the yield.…”