Regioselective Zn(OAc)2-catalyzed azide–alkyne cycloaddition in water: the green click-chemistry
Literature Information
Publication Date
2017-02-08
DOI
10.1039/C6QO00787B
Impact Factor
5.281
Authors
Maria A. Morozova, Mekhman S. Yusubov, Václav Eigner, Alexander A. Bondarev, Akio Saito, Marina E. Trusova, Pavel S. Postnikov
View Original
Abstract
A new method of azide–alkyne cycloaddition (AAC) in the presence of Zn(OAc)2 as an inexpensive and environmentally friendly catalyst in neat water has been developed. The proposed methodology has been applied for the synthesis of 1,4-disubstituted-1,2,3-triazoles from terminal alkynes and 1,4,5-trisubstituted-1,2,3-triazoles from internal alkynes. It has been found that Zn-catalyzed AAC is extremely sensitive to steric hindrance in acetylenes and a method of regioselective triazole ring formation has been proposed. Particularly important is the isolation and characterization of a relatively stable Zn-containing intermediate, which has been characterized by NMR and HRMS.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate
CAS Number:
211429-79-7
Molecular Formula:
C15H17NO3
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