Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, CH Insertion, and Dimerization Reactions

Mesityl gold(I) carbenes lacking heteroatom stabilization or shielding ancillary ligands have been generated and spectroscopically characterized from chloro(mesityl)methylgold(I) carbenoids bearing JohnPhos-type ligands by chloride abstraction with GaCl3. The aryl carbenes react with PPh3 and alkene...

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Autores: García-Morales, Cristina, Pei, Xiao-Li, Sarria Toro, Juan M., Echavarren, Antonio M.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/352279
Acceso en línea:http://hdl.handle.net/2072/352279
https://doi.org/10.1002/anie.201814577
Access Level:acceso abierto
Palabra clave:54
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spelling Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, CH Insertion, and Dimerization ReactionsGarcía-Morales, CristinaPei, Xiao-LiSarria Toro, Juan M.Echavarren, Antonio M.54Mesityl gold(I) carbenes lacking heteroatom stabilization or shielding ancillary ligands have been generated and spectroscopically characterized from chloro(mesityl)methylgold(I) carbenoids bearing JohnPhos-type ligands by chloride abstraction with GaCl3. The aryl carbenes react with PPh3 and alkenes to give stable phosphonium ylides and cyclopropanes, respectively. Oxidation with pyridine N-oxide and intermolecular CH insertion to cyclohexane have also been observed. In the absence of nucleophiles, a bimolecular reaction, similar to that observed for other metal carbenes, leads to a symmetrical alkene.2019info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion3957 p.application/vnd.openxmlformats-officedocument.wordprocessingml.documenthttp://hdl.handle.net/2072/352279https://doi.org/10.1002/anie.201814577RECERCAT (Dipòsit de la Recerca de Catalunya)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésL'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:2072/3522792026-05-29T05:05:01Z
dc.title.none.fl_str_mv Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, CH Insertion, and Dimerization Reactions
title Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, CH Insertion, and Dimerization Reactions
spellingShingle Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, CH Insertion, and Dimerization Reactions
García-Morales, Cristina
54
title_short Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, CH Insertion, and Dimerization Reactions
title_full Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, CH Insertion, and Dimerization Reactions
title_fullStr Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, CH Insertion, and Dimerization Reactions
title_full_unstemmed Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, CH Insertion, and Dimerization Reactions
title_sort Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, CH Insertion, and Dimerization Reactions
dc.creator.none.fl_str_mv García-Morales, Cristina
Pei, Xiao-Li
Sarria Toro, Juan M.
Echavarren, Antonio M.
author García-Morales, Cristina
author_facet García-Morales, Cristina
Pei, Xiao-Li
Sarria Toro, Juan M.
Echavarren, Antonio M.
author_role author
author2 Pei, Xiao-Li
Sarria Toro, Juan M.
Echavarren, Antonio M.
author2_role author
author
author
dc.subject.none.fl_str_mv 54
topic 54
description Mesityl gold(I) carbenes lacking heteroatom stabilization or shielding ancillary ligands have been generated and spectroscopically characterized from chloro(mesityl)methylgold(I) carbenoids bearing JohnPhos-type ligands by chloride abstraction with GaCl3. The aryl carbenes react with PPh3 and alkenes to give stable phosphonium ylides and cyclopropanes, respectively. Oxidation with pyridine N-oxide and intermolecular CH insertion to cyclohexane have also been observed. In the absence of nucleophiles, a bimolecular reaction, similar to that observed for other metal carbenes, leads to a symmetrical alkene.
publishDate 2019
dc.date.none.fl_str_mv 2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/352279
https://doi.org/10.1002/anie.201814577
url http://hdl.handle.net/2072/352279
https://doi.org/10.1002/anie.201814577
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 3957 p.
application/vnd.openxmlformats-officedocument.wordprocessingml.document
dc.source.none.fl_str_mv RECERCAT (Dipòsit de la Recerca de Catalunya)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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