dc.contributor.author | Holmsen, Marte Sofie | |
dc.contributor.author | Ihlefeldt, Franziska | |
dc.contributor.author | Øien-Ødegaard, Sigurd | |
dc.contributor.author | Langseth, Eirin | |
dc.contributor.author | Wencke, Yannick | |
dc.contributor.author | Heyn, Richard H. | |
dc.contributor.author | Tilset, Mats | |
dc.date.accessioned | 2020-12-17T13:00:58Z | |
dc.date.available | 2020-12-17T13:00:58Z | |
dc.date.created | 2018-07-26T11:40:32Z | |
dc.date.issued | 2018 | |
dc.identifier.citation | Organometallics. 2018, 37 (12), 1937-1947. | en_US |
dc.identifier.issn | 0276-7333 | |
dc.identifier.uri | https://hdl.handle.net/11250/2720066 | |
dc.description.abstract | The reactivity of Au(OAcF)2(tpy) (1, OAcF = OCOCF3; tpy = 2-(p-tolyl)pyridine) toward a wide variety of different alkenes with various substitution patterns and different oxygen-based nucleophiles has been investigated. These reactions are two-step processes where a ligand substitution is followed by a nucleophilic addition furnishing Au(III) complexes with C(sp3) ligands. In this work we have found that the reactions always occur trans to tpy-N while the OAcF ligand remains in place trans to tpy-C. The nucleophilic addition takes place exclusively at the most substituted side of the double bond, in a Markovnikov manner, and the nucleophilic addition occurs in an anti fashion as can be seen from the reaction with the 2,3-disubstituted alkene trans-2-hexene. This study has provided valuable insight into the scope and regiochemistry of Au(III) mediated nucleophilic additions, which is of great importance for further development of Au(III) catalysis and alkene functionalization. | en_US |
dc.language.iso | eng | en_US |
dc.publisher | ACS Publications | en_US |
dc.subject | Resonance structures | en_US |
dc.subject | Substitution reactions | en_US |
dc.subject | Addition reactions | en_US |
dc.subject | Ligands | en_US |
dc.subject | Hydrocarbons | en_US |
dc.title | Markovnikov at Gold: Nucleophilic Addition to Alkenes at Au(III) | en_US |
dc.type | Peer reviewed | en_US |
dc.type | Journal article | en_US |
dc.description.version | acceptedVersion | en_US |
dc.rights.holder | This document is the accepted manuscript version of a published work that appeared in final form in Organometallics, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.organomet.8b00218 | en_US |
dc.source.pagenumber | 1937-1947 | en_US |
dc.source.volume | 37 | en_US |
dc.source.journal | Organometallics | en_US |
dc.source.issue | 12 | en_US |
dc.identifier.doi | 10.1021/acs.organomet.8b00218 | |
dc.identifier.cristin | 1598723 | |
cristin.unitcode | 7401,80,40,0 | |
cristin.unitname | Prosessteknologi | |
cristin.ispublished | true | |
cristin.fulltext | postprint | |
cristin.qualitycode | 2 | |