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Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction
Author(s) -
JuanCarlos Castillo,
Néstor-Fabián Bravo,
Lenka-Victoria Tamayo,
Paula Daniela Mestizo,
John Hurtado,
Mario A. Macías,
Jaime Portilla
Publication year - 2020
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.0c04592
Subject(s) - catalysis , alkyne , click chemistry , yield (engineering) , substrate (aquarium) , chemistry , combinatorial chemistry , alkyl , sodium azide , atom economy , materials science , organic chemistry , composite material , oceanography , geology
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.

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