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Copper(0) nanoparticle catalyzed Z ‐Selective Transfer Semihydrogenation of Internal Alkynes
Author(s) -
Moran Maria Jesus,
Martina Katia,
Bieliunas Vidmantas,
Baricco Francesca,
Tagliapietra Silvia,
Berlier Gloria,
De Borggraeve Wim M.,
Cravotto Giancarlo
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100126
Subject(s) - chemistry , chemoselectivity , catalysis , transfer hydrogenation , ethylene glycol , nanoparticle , copper , photochemistry , combinatorial chemistry , organic chemistry , chemical engineering , ruthenium , engineering
Abstract The use of copper(0) nanoparticles in the transfer semihydrogenation of alkynes has been investigated as a lead‐free alternative to Lindlar catalysts. A stereo‐selective methodology for the hydrogenation of internal alkynes to the corresponding ( Z )‐alkenes in high isolated yields (86% average) has been developed. This green and sustainable transfer hydrogenation protocol relies on non‐noble copper nanoparticles for reduction of both electron‐rich and electron‐deficient, aliphatic‐substituted and aromatic‐ substituted internal alkynes. Polyols, such as ethylene glycol and glycerol, have been proven to act as hydrogen sources, and excellent stereo‐ and chemoselectivity have been observed. Enabling technologies, such as microwave and ultrasound irradiation are shown to enhance heat and mass transfer, whether used alone or in combination, resulting in a decrease in reaction time from hours to minutes.