dc.contributor.author | Papastavrou, Argyro T. | |
dc.contributor.author | Pauze, Martin Paule | |
dc.contributor.author | Gómez Bengoa, Enrique | |
dc.contributor.author | Vougioukalakis, Georgios C | |
dc.date.accessioned | 2021-07-07T13:04:59Z | |
dc.date.available | 2021-07-07T13:04:59Z | |
dc.date.issued | 2019-02-19 | |
dc.identifier.citation | ChemCatChem 11(21) : 5379-5386 (2019) | es_ES |
dc.identifier.issn | 1867-3880 | |
dc.identifier.uri | http://hdl.handle.net/10810/52180 | |
dc.description.abstract | An efficient and straightforward organocatalytic method for the
direct, multicomponent carboxylation of terminal alkynes with
CO2 and organochlorides, towards propargylic esters, is reported
for the first time. 1,3-Di-tert-butyl-1H-imidazol-3-ium
chloride, a simple, widely-available, stable, and cost-efficient Nheterocyclic
carbene (NHC) precursor salt was used as the (pre)
catalyst. A wide range of phenylacetylenes, bearing electronwithdrawing
or electron-donating substituents, react with allylchlorides,
benzyl chlorides, or 2-chloroacetates, providing the
corresponding propargylic esters in low to excellent yields. DFT
calculations on the mechanism of this transformation indicate
that the reaction is initiated with the formation of an NHCcarboxylate,
by addition of the carbene to a molecule of CO2.
Then, the nucleophilic addition of this species to the corresponding
chlorides has been computed to be the rate limiting
step of the process | es_ES |
dc.description.sponsorship | We acknowledge the contribution of COST Action CA15106 (C−H Activation in Organic Synthesis-CHAOS). The Special Account for Research Grants of the National and Kapodistrian University of Athens is also gratefully acknowledged for funding (Research Program 70/3/14872). Moreover, we are thankful for the technical and human support provided by IZO-SGI SGIker of UPV/EHU, and the European Funding Horizon 2020-MSCA (ITN-EJD CATMEC 14/06-721223) | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Wiley‐VCH | es_ES |
dc.relation | info:eu-repo/grantAgreement/EC/H2020/721223 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.title | Unprecedented Multicomponent Organocatalytic Synthesis of Propargylic Esters via CO2 Activation | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim | es_ES |
dc.relation.publisherversion | https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cctc.201900207 | es_ES |
dc.identifier.doi | 10.1002/cctc.201900207 | |
dc.contributor.funder | European Commission | |
dc.departamentoes | Química orgánica I | es_ES |
dc.departamentoeu | Kimika organikoa I | es_ES |