An N-heterocyclic carbene ligand promotes highly selective alkyne semihydrogenation with copper nanoparticles supported on passivated silica

Chemical Science
Nicolas KaefferChristophe Copéret

Abstract

We report a surface organometallic route that generates copper nanoparticles (NPs) on a silica support while simultaneously passivating the silica surface with trimethylsiloxy groups. The material is active for the catalytic semihydrogenation of phenylalkyl-, dialkyl- and diaryl-alkynes and displays high chemo- and stereoselectivity at full alkyne conversion to corresponding (Z)-olefins in the presence of an N-heterocyclic carbene (NHC) ligand. Solid-state NMR spectroscopy using the NHC ligand 13C-labeled at the carbenic carbon reveals a genuine coordination of the carbene to Cu NPs. The presence of distinct Cu surface environments and the coordination of the NHC to specific Cu sites likely account for the increased selectivity.

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Citations

Jun 18, 2019·Chemistry : a European Journal·Xavier FrogneuxSophie Carenco
Apr 13, 2019·ChemSusChem·Kathiravan MurugesanMatthias Beller
Oct 23, 2019·Chemical Communications : Chem Comm·Trinadh KaicharlaJohannes F Teichert
May 5, 2021·Journal of the American Chemical Society·Scott R Docherty, Christophe Copéret
Jun 22, 2021·Chemical Communications : Chem Comm·Byoung Yong ParkMin Su Han
Jul 11, 2021·The Review of Scientific Instruments·Chase A SalazarShannon S Stahl
Mar 17, 2020·ACS Applied Materials & Interfaces·Bryce A TappanRichard L Brutchey

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Methods Mentioned

BETA
NMR
X-ray

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