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Sonogashira cross-coupling over Au(1 1 1): from UHV to ambient pressure

Johansson, Niclas LU ; Sisodiya, Sheetal LU ; Shayesteh, Payam LU ; Chaudhary, Shilpi LU ; Andersen, Jesper N LU ; Knudsen, Jan LU ; Wendt, Ola LU and Schnadt, Joachim LU (2017) In Journal of Physics: Condensed Matter1990-01-01+01:00 29(44).
Abstract
We have studied the reaction of phenylacetylene (PA) with chloro-, bromo-, and iodobenzene on the Au(1 1 1) surface as a model system for the gold-catalysed Sonogashira cross-coupling. Both ultrahigh vacuum-based and ambient pressure x-ray photoelectron spectroscopy show that iodo- and chlorobenzene (IB and CB) undergo the cross-coupling reaction towards diphenylacetylene. Bromobenzene (BB), in contrast, does not react in the UHV experiments. Further, at ambient pressure signs are found for poisoning of the Au(1 1 1) surface by a carbon species formed in the reaction. The understanding obtained in the reaction experiments are based on a thorough investigation of the adsorption of PA, IB, CB, and BB on the Au(1 1 1) surface by soft x-ray... (More)
We have studied the reaction of phenylacetylene (PA) with chloro-, bromo-, and iodobenzene on the Au(1 1 1) surface as a model system for the gold-catalysed Sonogashira cross-coupling. Both ultrahigh vacuum-based and ambient pressure x-ray photoelectron spectroscopy show that iodo- and chlorobenzene (IB and CB) undergo the cross-coupling reaction towards diphenylacetylene. Bromobenzene (BB), in contrast, does not react in the UHV experiments. Further, at ambient pressure signs are found for poisoning of the Au(1 1 1) surface by a carbon species formed in the reaction. The understanding obtained in the reaction experiments are based on a thorough investigation of the adsorption of PA, IB, CB, and BB on the Au(1 1 1) surface by soft x-ray absorption spectroscopy and temperature-dependent x-ray photoelectron spectroscopy. In particular, the experiments provide the orientation of the intact adsorbates with respect to the surfaces at liquid nitrogen temperature. Dissociation in the temperature regime between  −80 and  −15 °C is observed for iodo- and chlorobenzene, but not for BB, in agreement with that only IB and CB, but not BB, react with PA to form diphenylacetylene. The difference is tentatively attributed to a difference in surface orientation of the different halobenzenes. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Au(111), halobenzene, XPS, XAS, APXPS, Sonogashira cross-coupling
in
Journal of Physics: Condensed Matter1990-01-01+01:00
volume
29
issue
44
publisher
IOP Publishing
external identifiers
  • scopus:85037675317
  • wos:000412410400005
ISSN
1361-648X
DOI
10.1088/1361-648X/aa89c4
language
English
LU publication?
yes
id
9c6591d2-7314-41cc-ae30-5f14b78cf556
date added to LUP
2017-10-13 16:16:54
date last changed
2018-08-08 09:12:04
@article{9c6591d2-7314-41cc-ae30-5f14b78cf556,
  abstract     = {We have studied the reaction of phenylacetylene (PA) with chloro-, bromo-, and iodobenzene on the Au(1 1 1) surface as a model system for the gold-catalysed Sonogashira cross-coupling. Both ultrahigh vacuum-based and ambient pressure x-ray photoelectron spectroscopy show that iodo- and chlorobenzene (IB and CB) undergo the cross-coupling reaction towards diphenylacetylene. Bromobenzene (BB), in contrast, does not react in the UHV experiments. Further, at ambient pressure signs are found for poisoning of the Au(1 1 1) surface by a carbon species formed in the reaction. The understanding obtained in the reaction experiments are based on a thorough investigation of the adsorption of PA, IB, CB, and BB on the Au(1 1 1) surface by soft x-ray absorption spectroscopy and temperature-dependent x-ray photoelectron spectroscopy. In particular, the experiments provide the orientation of the intact adsorbates with respect to the surfaces at liquid nitrogen temperature. Dissociation in the temperature regime between  −80 and  −15 °C is observed for iodo- and chlorobenzene, but not for BB, in agreement with that only IB and CB, but not BB, react with PA to form diphenylacetylene. The difference is tentatively attributed to a difference in surface orientation of the different halobenzenes.},
  articleno    = {444005},
  author       = {Johansson, Niclas and Sisodiya, Sheetal and Shayesteh, Payam and Chaudhary, Shilpi and Andersen, Jesper N and Knudsen, Jan and Wendt, Ola and Schnadt, Joachim},
  issn         = {1361-648X},
  keyword      = {Au(111),halobenzene,XPS,XAS,APXPS,Sonogashira cross-coupling},
  language     = {eng},
  month        = {10},
  number       = {44},
  publisher    = {IOP Publishing},
  series       = {Journal of Physics: Condensed Matter1990-01-01+01:00},
  title        = {Sonogashira cross-coupling over Au(1 1 1): from UHV to ambient pressure},
  url          = {http://dx.doi.org/10.1088/1361-648X/aa89c4},
  volume       = {29},
  year         = {2017},
}