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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.

Sonogashira Cross-Coupling and Homocoupling on a Silver Surface: Chlorobenzene and Phenylacetylene on Ag(100) Thumbnail


Authors

Carlos Sanchez-Sanchez

Noe Orozco

Juan P. Holgado

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 Mar 28, 2024
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

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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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