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Efficient alkyne homocoupling catalysed by copper immobilized on functionalized silica
Author(s) -
Gelderen Laurens,
Rothenberg Gadi,
Roberto Calderone V.,
Wilson Karen,
Raveendran Shiju N.
Publication year - 2013
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.2933
Subject(s) - chemistry , alkyne , catalysis , copper , reagent , leaching (pedology) , x ray photoelectron spectroscopy , heterogeneous catalysis , oxidative coupling of methane , coupling reaction , polymer chemistry , combinatorial chemistry , organic chemistry , chemical engineering , environmental science , soil science , engineering , soil water
Copper immobilized on a functionalized silica support is a good catalyst for the homocoupling of terminal alkynes. The so‐called Glaser–Hay coupling reaction can be run in air with catalytic amounts of base. The copper catalyst is active for multiple substituted alkynes, in both polar and non‐polar solvents, with good to excellent yields (75–95%). Depending on the alkyne, full conversion can be achieved within 3–24 h. The catalyst was characterized by TGA, inductively coupled plasma and X‐ray photoelectron spectroscopy . Leaching tests confirm that the catalyst is and remains heterogeneous. Importantly, the overall reaction requires only alkyne and oxygen (in this case, air) as reagents, making this a clean catalytic oxidative coupling reaction . Copyright © 2012 John Wiley & Sons, Ltd.