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Azide–Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex
Author(s) -
Topchiy Maxim A.,
Ageshina Alexandra A.,
Gribanov Pavel S.,
Masoud Salekh M.,
Akmalov Timur R.,
Nefedov Sergey E.,
Osipov Sergey N.,
Nechaev Mikhail S.,
Asachenko Andrey F.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801538
Subject(s) - chemistry , alkyne , cycloaddition , catalysis , azide , alkane , combinatorial chemistry , cyclohexane , copper , heptane , organic chemistry , polymer chemistry
A highly efficient and environmentally benign protocol for copper‐catalyzed alkyne–azide cycloaddition (CuAAC) in industrially important alkane solvents was developed. New copper(I) complexes bearing NHC ligands decorated with bulky hexafluoroisopropylalkoxy group [(CF 3 ) 2 (OR)C‐] were first introduced for the process. The complex with isopentyl group [(CF 3 ) 2 (O i Am)C‐] exhibited the best catalytic activity in the reactions of diversely substituted alkyne and azide substrates in alkane solvents, such as hexane, heptane and cyclohexane. The new CuAAC protocol is easily scalable, synthetically robust, and reproducible; it utilizes low catalyst loadings and enables simple isolation of pure products free from any contaminants including residue of the catalyst and starting materials.