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Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction.


ABSTRACT: A new monophosphine Cu(I) complex bearing bis(pyrazolyl)methane (L 1 ) (CuIL 1 PPh 3 ) was synthesized and used as a catalyst for the three-component click reaction from an alkyl halide, sodium azide, and terminal alkyne to furnish 1,4-disubstituted 1,2,3-triazoles in up to 93% yield. The catalyst is highly stable, compatible with oxygen/water, and works with total efficiency under ultrasonic condition. The structure of the complex was studied and confirmed by X-ray crystallography, finding a riveting relationship with its catalytic activity. This sustainable triazoles synthesis is distinguished by its high atom economy, low catalyst loading (up to 0.5 mol %), broad substrate scope, short reaction times, operational simplicity, and an easy gram-scale supply of a functionalized product for subsequent synthetic applications.

SUBMITTER: Castillo JC 

PROVIDER: S-EPMC7689893 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction.

Castillo Juan-Carlos JC   Bravo Nestor-Fabian NF   Tamayo Lenka-Victoria LV   Mestizo Paula-Daniela PD   Hurtado John J   Macías Mario M   Portilla Jaime J  

ACS omega 20201112 46


A new monophosphine Cu(I) complex bearing <i>bis</i>(pyrazolyl)methane (<b>L</b> <sub><b>1</b></sub> ) (<b>CuIL</b> <sub><b>1</b></sub> <b>PPh</b> <sub><b>3</b></sub> ) was synthesized and used as a catalyst for the three-component click reaction from an alkyl halide, sodium azide, and terminal alkyne to furnish 1,4-disubstituted 1,2,3-triazoles in up to 93% yield. The catalyst is highly stable, compatible with oxygen/water, and works with total efficiency under ultrasonic condition. The structu  ...[more]

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