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A layered double hydroxide, a synthetically useful heterogeneous catalyst for azide−alkyne cycloadditions in a continuous-flow reactor

Paper ID Volume ID Publish Year Pages File Format Full-Text
39157 45809 2015 11 PDF Available
Title
A layered double hydroxide, a synthetically useful heterogeneous catalyst for azide−alkyne cycloadditions in a continuous-flow reactor
Abstract

•Cu(II)Fe(III)-based-layered double hydroxide was prepared and fully characterized.•The as-prepared material was highly active as catalyst in alkyne–azide cycloadditions.•The catalytic capabilities were investigated in continuo under high-p/T conditions.•No decrease of activity or destruction of the catalyst structure arose upon scaling-up.•Formation of reversible lattice defects was responsible for the observed activity.

A Cu(II)Fe(III)-layered double hydroxide is shown to efficiently catalyze 1,3-dipolar cycloadditions of organic azides to alkynes leading to valuable 1,2,3-triazoles. The benefits of continuous processing were exploited for reaction optimization and synthesis, and the production of triazoles was realized in an inherently safe and scalable manner. It was established that the catalytic activity of the as-prepared material can be derived from in situ reduction of Cu(II), generating lattice defects containing the catalytically active Cu(I) species. It was verified that oxidative homocoupling of the alkyne component was responsible for the conversion of Cu(II) to Cu(I), but a cooperation of certain structural items of the hydrotalcite-like material could also contribute to the outstanding catalytic efficiency. After a successful gram-scale triazole synthesis under high-pressure/high-temperature conditions, no destruction of the catalyst structure was found, suggesting that the layered double hydroxide acted as a highly robust catalytic system.

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Keywords
Layered double hydroxide; Continuous-flow processing; 1,3-Dipolar alkyne–azide cycloaddition; Copper ions
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A layered double hydroxide, a synthetically useful heterogeneous catalyst for azide−alkyne cycloadditions in a continuous-flow reactor
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 501, 25 July 2015, Pages 63–73
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Don't Miss Today's Special Offer
Price was $35.95
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Price after discount Only $4.95
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