Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones

We report a new catalytic protocol for the synthesis of γ,δ-unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass...

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Autores: Gómez-Suárez, Adrián, Gasperini, Danila, Vummaleti, Sai Vikrama Chaitanya, Poater Teixidor, Albert, Cavallo, Luigi, Nolan, Steven P.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2014
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:10256/10346
Acceso en línea:http://hdl.handle.net/10256/10346
Access Level:acceso embargado
Palabra clave:Cetones -- Síntesi
Ketones -- Synthesis
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spelling Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketonesGómez-Suárez, AdriánGasperini, DanilaVummaleti, Sai Vikrama ChaitanyaPoater Teixidor, AlbertCavallo, LuigiNolan, Steven P.Cetones -- SíntesiKetones -- SynthesisWe report a new catalytic protocol for the synthesis of γ,δ-unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass efficiency) than the previous state-of-the-art technique. In addition, this method tolerates both terminal and internal alkynes. Moreover, computational studies have been carried out in order to shed light on how the Claisen rearrangement is initiatedThe ERC (Advanced Investigator Award-FUNCAT), EPSRC and Syngenta are gratefully acknowledged for support. Umicore AG is acknowledged for their generous gift of materials. The EPSRC National Mass Spectrometry Service Centre (NMSSC) is gratefully acknowledged for HRMS analyses. S.P.N. is a Royal Society Wolfson Research Merit Award holder. S.P.N. and L.C. thank King Abdullah University of Science and Technology (CCF project) for support. L.C. thanks the HPC team of Enea for using the ENEA-GRID and the HPC facilities CRESCO in Portici (Italy) for access to remarkable computational resources. A.P. thanks the Spanish MINECO for a Ramon y Cajal contract (RYC-2009-05226) and European Commission for a Career Integration Grant (CIG09-GA-2011-293900)American Chemical Society (ACS)Ministerio de Ciencia e Innovación (Espanya)infoinfo2014info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10256/10346http://hdl.handle.net/10256/10346© ACS Catalysis, 2014, vol. 4, p. 2701-2705Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1021/cs500806minfo:eu-repo/semantics/altIdentifier/issn/2155-5435info:eu-repo/grantAgreement/MICINN//RYC-2009-05226info:eu-repo/grantAgreement/EC/FP7/293900Tots els drets reservatsinfo:eu-repo/semantics/embargoedAccessoai:recercat.cat:10256/103462026-05-29T05:05:01Z
dc.title.none.fl_str_mv Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones
title Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones
spellingShingle Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones
Gómez-Suárez, Adrián
Cetones -- Síntesi
Ketones -- Synthesis
title_short Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones
title_full Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones
title_fullStr Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones
title_full_unstemmed Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones
title_sort Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones
dc.creator.none.fl_str_mv Gómez-Suárez, Adrián
Gasperini, Danila
Vummaleti, Sai Vikrama Chaitanya
Poater Teixidor, Albert
Cavallo, Luigi
Nolan, Steven P.
author Gómez-Suárez, Adrián
author_facet Gómez-Suárez, Adrián
Gasperini, Danila
Vummaleti, Sai Vikrama Chaitanya
Poater Teixidor, Albert
Cavallo, Luigi
Nolan, Steven P.
author_role author
author2 Gasperini, Danila
Vummaleti, Sai Vikrama Chaitanya
Poater Teixidor, Albert
Cavallo, Luigi
Nolan, Steven P.
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (Espanya)
dc.subject.none.fl_str_mv Cetones -- Síntesi
Ketones -- Synthesis
topic Cetones -- Síntesi
Ketones -- Synthesis
description We report a new catalytic protocol for the synthesis of γ,δ-unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass efficiency) than the previous state-of-the-art technique. In addition, this method tolerates both terminal and internal alkynes. Moreover, computational studies have been carried out in order to shed light on how the Claisen rearrangement is initiated
publishDate 2014
dc.date.none.fl_str_mv 2014
info
info
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/10346
http://hdl.handle.net/10256/10346
url http://hdl.handle.net/10256/10346
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/cs500806m
info:eu-repo/semantics/altIdentifier/issn/2155-5435
info:eu-repo/grantAgreement/MICINN//RYC-2009-05226
info:eu-repo/grantAgreement/EC/FP7/293900
dc.rights.none.fl_str_mv Tots els drets reservats
info:eu-repo/semantics/embargoedAccess
rights_invalid_str_mv Tots els drets reservats
eu_rights_str_mv embargoedAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society (ACS)
publisher.none.fl_str_mv American Chemical Society (ACS)
dc.source.none.fl_str_mv © ACS Catalysis, 2014, vol. 4, p. 2701-2705
Articles publicats (D-Q)
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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score 15.812429

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