Please use this identifier to cite or link to this item:
https://hdl.handle.net/10316/103391
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Felgueiras, Alexandre P. | - |
dc.contributor.author | Rodrigues, Fábio M. S. | - |
dc.contributor.author | Carrilho, Rui M. B. | - |
dc.contributor.author | Cruz, Pedro F. | - |
dc.contributor.author | Rodrigues, Vítor H. | - |
dc.contributor.author | Kégl, Tamás | - |
dc.contributor.author | Kollár, László | - |
dc.contributor.author | Pereira, Mariette M. | - |
dc.date.accessioned | 2022-11-10T12:10:04Z | - |
dc.date.available | 2022-11-10T12:10:04Z | - |
dc.date.issued | 2022-03-19 | - |
dc.identifier.issn | 1420-3049 | pt |
dc.identifier.uri | https://hdl.handle.net/10316/103391 | - |
dc.description.abstract | Four stereoisomeric monoether derivatives, based on axially chiral (R)- or (S)-BINOL bearing a chiral (+)- or (-)-neomenthyloxy group were synthesised and fully characterised by NMR spectroscopy and X-ray crystallography. The respective tris-monophosphites were thereof prepared and fully characterised. The coordination ability of the new bulky phosphites with Rh(CO)2(acac), was attested by 31P NMR, which presented a doublet in the range of δ = 120 ppm, with a 1J(103Rh-31P) coupling constant of 290 Hz. The new tris-binaphthyl phosphite ligands were further characterised by DFT computational methods, which allowed us to calculate an electronic (CEP) parameter of 2083.2 cm-1 and an extremely large cone angle of 345°, decreasing to 265° upon coordination with a metal atom. Furthermore, the monophosphites were applied as ligands in rhodium-catalysed hydroformylation of styrene, leading to complete conversions in 4 h, 100% chemoselectivity for aldehydes and up to 98% iso-regioselectivity. The Rh(I)/phosphite catalytic system was also highly active and selective in the hydroformylation of disubstituted olefins, including (E)-prop-1-en-1-ylbenzene and prop-1-en-2-ylbenzene. | pt |
dc.language.iso | eng | pt |
dc.relation | UIDB/00313/2020 | pt |
dc.relation | UIDP/00313/2020 | pt |
dc.relation | PTDC/QUI-OUT/27996/2017 (DUALPI) | pt |
dc.relation | CENTRO-07-CT62-FEDER-002012 (UC-NMR) | pt |
dc.relation | NKFIH within the framework of the project TKP2021-EGA-17 | pt |
dc.rights | openAccess | pt |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | pt |
dc.subject | BINOL | pt |
dc.subject | menthol | pt |
dc.subject | X-ray diffraction | pt |
dc.subject | monophosphite synthesis | pt |
dc.subject | Mitsunobu reaction | pt |
dc.subject | DFT computational methods | pt |
dc.subject | Tolman’s cone angle | pt |
dc.subject | computed electronic parameter (CEP) | pt |
dc.subject | rhodiumcatalysed hydroformylation | pt |
dc.title | Stereoisomeric Tris-BINOL-Menthol Bulky Monophosphites: Synthesis, Characterisation and Application in Rhodium-Catalysed Hydroformylation | pt |
dc.type | article | - |
degois.publication.firstPage | 1989 | pt |
degois.publication.issue | 6 | pt |
degois.publication.title | Molecules | pt |
dc.peerreviewed | yes | pt |
dc.identifier.doi | 10.3390/molecules27061989 | pt |
degois.publication.volume | 27 | pt |
dc.date.embargo | 2022-03-19 | * |
uc.date.periodoEmbargo | 0 | pt |
item.grantfulltext | open | - |
item.fulltext | Com Texto completo | - |
item.openairetype | article | - |
item.languageiso639-1 | en | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.cerifentitytype | Publications | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CFisUC – Center for Physics of the University of Coimbra | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.orcid | 0000-0002-1085-2720 | - |
crisitem.author.orcid | 0000-0001-9923-359X | - |
crisitem.author.orcid | 0000-0003-3578-0134 | - |
crisitem.author.orcid | 0000-0002-5164-1209 | - |
crisitem.author.orcid | 0000-0003-4958-7677 | - |
Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais |
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Stereoisomeric-TrisBINOLMenthol-Bulky-Monophosphites-Synthesis-Characterisation-and-Application-in-RhodiumCatalysed-HydroformylationMolecules.pdf | 2.5 MB | Adobe PDF | View/Open |
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