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Practical one‐pot synthesis of 5‐alkynyl‐1,2,3‐triazoles via heterogeneous copper(I)‐catalyzed tandem three‐component click/alkynylation reaction
Author(s) -
Zhao Ruonan,
Liao Yang,
Yan Tao,
Cai Mingzhong
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5319
Subject(s) - chemistry , catalysis , reagent , tandem , combinatorial chemistry , copper , alkynylation , click chemistry , heterogeneous catalysis , cascade reaction , filtration (mathematics) , reaction conditions , organic chemistry , materials science , composite material , statistics , mathematics
An efficient and practical route to 5‐alkynyl‐1,2,3‐triazoles has been developed via heterogeneous tandem CuAAC/alkynylation reaction of organic azides, alkynes and 1‐bromoalkynes by using an L ‐proline‐functionalized MCM‐41‐anchored copper(I) complex [ L ‐Proline‐MCM‐41‐CuCl] as catalyst under mild conditions. The reaction produces a wide variety of 5‐alkynyl‐1,2,3‐triazoles in mostly good to excellent yields. The new immobilized copper(I) complex can be readily prepared from commercially available and inexpensive reagents and displays the same catalytic activity as CuCl. The L ‐Proline‐MCM‐41‐CuCl catalyst is also easy to recover via a simple filtration process and can be reused at least seven times without apparent loss of activity.