Copper(II)-Catalyzed Aerobic Oxidative Synthesis of Substituted 1,2,3- and 1,2,4-Triazoles from Bisarylhydrazones via C–H Functionalization/C–C/N–N/C–N Bonds Formation

An unprecedented copper(II)-catalyzed aerobic oxidative synthesis of 2,4,5-triaryl-1,2,3-triazoles and 1,3,5-triaryl-1,2,4-triazoles from bisarylhydrazones as the common starting precursor has been achieved via cascade C–H functionalization/C–C/N–N/C–N bonds formation under mild reaction conditions....

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Bibliographic Details
Published in:Journal of organic chemistry 2012-06, Vol.77 (11), p.5063-5073
Main Authors: Guru, Murali Mohan, Punniyamurthy, Tharmalingam
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:An unprecedented copper(II)-catalyzed aerobic oxidative synthesis of 2,4,5-triaryl-1,2,3-triazoles and 1,3,5-triaryl-1,2,4-triazoles from bisarylhydrazones as the common starting precursor has been achieved via cascade C–H functionalization/C–C/N–N/C–N bonds formation under mild reaction conditions. One of the enthralling outcomes of this strategy is the copper(II)-catalyzed room temperature C–H functionalization/C–N bond formation in presence of air, which has been accomplished during the synthesis of substituted 1,2,4-triazoles. This new class of compounds could give prospective luminescence as an iconic component in the area of pharmaceutical and biological sciences. The intermediates for both the processes have been isolated to elucidate the mechanistic scenario.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300592t