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Terminal alkyne coupling reactions through a ring : mechanistic insights and regiochemical switching
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Storey, Caroline M., Gyton, Matthew R., Andrew, Rhiann E. and Chaplin, Adrian B. (2018) Terminal alkyne coupling reactions through a ring : mechanistic insights and regiochemical switching. Angewandte Chemie International Edition, 57 (37). pp. 12003-12006. doi:10.1002/anie.201807028 ISSN 1433-7851.
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Official URL: http://dx.doi.org/10.1002/anie.201807028
Abstract
The mechanism and selectivity of terminal alkyne coupling reactions promoted by Rh(I) complexes of NHC‐based CNC pincer ligands have been investigated. Synthetic and kinetic experiments support E‐ and gem‐enyne formation through a common reaction sequence involving hydrometallation and rate determining C‐C bond reductive elimination. The latter is significantly affected by the ligand topology: employment of a macrocyclic variant enforces exclusive head‐to‐head coupling, contrasting the high selectivity for head‐to‐tail coupling observed for the corresponding acyclic pincer.
| Item Type: | Journal Article | |||||||||||||||||||||
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| Subjects: | Q Science > QD Chemistry | |||||||||||||||||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||||||||||||||
| Library of Congress Subject Headings (LCSH): | Alkynes, Transition metal compounds, Catalysis, Ligands | |||||||||||||||||||||
| Journal or Publication Title: | Angewandte Chemie International Edition | |||||||||||||||||||||
| Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | |||||||||||||||||||||
| ISSN: | 1433-7851 | |||||||||||||||||||||
| Official Date: | 10 September 2018 | |||||||||||||||||||||
| Dates: |
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| Volume: | 57 | |||||||||||||||||||||
| Number: | 37 | |||||||||||||||||||||
| Page Range: | pp. 12003-12006 | |||||||||||||||||||||
| DOI: | 10.1002/anie.201807028 | |||||||||||||||||||||
| Status: | Peer Reviewed | |||||||||||||||||||||
| Publication Status: | Published | |||||||||||||||||||||
| Access rights to Published version: | Open Access (Creative Commons) | |||||||||||||||||||||
| Date of first compliant deposit: | 17 July 2018 | |||||||||||||||||||||
| Date of first compliant Open Access: | 18 October 2018 | |||||||||||||||||||||
| RIOXX Funder/Project Grant: |
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