Issue 24, 2018

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

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
27 Apr 2018
Accepted
23 May 2018
First published
23 May 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 5366-5371

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

N. Kaeffer, H. Liu, H. Lo, A. Fedorov and C. Copéret, Chem. Sci., 2018, 9, 5366 DOI: 10.1039/C8SC01924J

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