Carlos Sanchez-Sanchez
Sonogashira Cross-Coupling and Homocoupling on a Silver Surface: Chlorobenzene and Phenylacetylene on Ag(100)
Sanchez-Sanchez, Carlos; Orozco, Noe; Holgado, Juan P.; Beaumont, Simon K.; Kyriakou, Georgios; Watson, David J.; Gonzalez-Elipe, Agustin R.; Feria, Leticia; Fernández Sanz, Javier; Lambert, Richard M.
Authors
Noe Orozco
Juan P. Holgado
Dr Simon Beaumont simon.beaumont@durham.ac.uk
Associate Professor
Georgios Kyriakou
David J. Watson
Agustin R. Gonzalez-Elipe
Leticia Feria
Javier Fernández Sanz
Richard M. Lambert
Abstract
Scanning tunneling microscopy, temperature-programmed reaction, near-edge X-ray absorption fine structure spectroscopy, and density functional theory calculations were used to study the adsorption and reactions of phenylacetylene and chlorobenzene on Ag(100). In the absence of solvent molecules and additives, these molecules underwent homocoupling and Sonogashira cross-coupling in an unambiguously heterogeneous mode. Of particular interest is the use of silver, previously unexplored, and chlorobenzene—normally regarded as relatively inert in such reactions. Both molecules adopt an essentially flat-lying conformation for which the observed and calculated adsorption energies are in reasonable agreement. Their magnitudes indicate that in both cases adsorption is predominantly due to dispersion forces for which interaction nevertheless leads to chemical activation and reaction. Both adsorbates exhibited pronounced island formation, thought to limit chemical activity under the conditions used and posited to occur at island boundaries, as was indeed observed in the case of phenylacetylene. The implications of these findings for the development of practical catalytic systems are considered.
Citation
Sanchez-Sanchez, C., Orozco, N., Holgado, J. P., Beaumont, S. K., Kyriakou, G., Watson, D. J., …Lambert, R. M. (2015). Sonogashira Cross-Coupling and Homocoupling on a Silver Surface: Chlorobenzene and Phenylacetylene on Ag(100). Journal of the American Chemical Society, 137(2), 940-947. https://doi.org/10.1021/ja5115584
Journal Article Type | Article |
---|---|
Online Publication Date | Jan 5, 2015 |
Publication Date | Jan 21, 2015 |
Deposit Date | Jan 13, 2015 |
Publicly Available Date | Jan 21, 2015 |
Journal | Journal of the American Chemical Society |
Print ISSN | 0002-7863 |
Electronic ISSN | 1520-5126 |
Publisher | American Chemical Society |
Peer Reviewed | Peer Reviewed |
Volume | 137 |
Issue | 2 |
Pages | 940-947 |
DOI | https://doi.org/10.1021/ja5115584 |
Public URL | https://durham-repository.worktribe.com/output/1438777 |
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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © 2014 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ja5115584.
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