Sonogashira cross-coupling over Au(1 1 1): from UHV to ambient pressure
(2017) In Journal of Physics: Condensed Matter 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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/9c6591d2-7314-41cc-ae30-5f14b78cf556
- author
- 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
- organization
- publishing date
- 2017-10-05
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Au(111), halobenzene, XPS, XAS, APXPS, Sonogashira cross-coupling
- in
- Journal of Physics: Condensed Matter
- volume
- 29
- issue
- 44
- article number
- 444005
- publisher
- IOP Publishing
- external identifiers
-
- pmid:28862150
- 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
- 2022-04-25 03:14:51
@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.}}, 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}}, keywords = {{Au(111); halobenzene; XPS; XAS; APXPS; Sonogashira cross-coupling}}, language = {{eng}}, month = {{10}}, number = {{44}}, publisher = {{IOP Publishing}}, series = {{Journal of Physics: Condensed Matter}}, title = {{Sonogashira cross-coupling over Au(1 1 1): from UHV to ambient pressure}}, url = {{http://dx.doi.org/10.1088/1361-648X/aa89c4}}, doi = {{10.1088/1361-648X/aa89c4}}, volume = {{29}}, year = {{2017}}, }