Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene

Handle URI:
http://hdl.handle.net/10754/600135
Title:
Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene
Authors:
Despagnet-Ayoub, Emmanuelle; Miqueu, Karinne; Sotiropoulos, Jean-Marc; Henling, Lawrence M.; Day, Michael W.; Labinger, Jay A.; Bercaw, John E.
Abstract:
Starting from the same ethylenediamine species, three valuable carbene precursors were synthesized under differing conditions: a tridentate dianionic N-heterocyclic carbene bearing an aniline, a phenol and a central dihydroimidazolium salt, its benzimidazolium isomer by intramolecular rearrangement and a dicationic benzimidazolium-benzoxazolium salt by changing the Brønsted acid from HCl to HBF4. A DFT study was performed to understand the rearrangement pathway. The structure of a bis[(NCO)carbene] zirconium complex was determined. © 2013 The Royal Society of Chemistry.
Citation:
Despagnet-Ayoub E, Miqueu K, Sotiropoulos J-M, Henling LM, Day MW, et al. (2013) Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene. Chem Sci 4: 2117. Available: http://dx.doi.org/10.1039/c3sc22171g.
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Chemical Science
Issue Date:
2013
DOI:
10.1039/c3sc22171g
Type:
Article
ISSN:
2041-6520; 2041-6539
Sponsors:
This work was supported by a KAUST Center-In-Development Grant to King Fahd University of Petroleum and Minerals (Dhahran, Saudi Arabia) and the USDOE Office of Basic Energy Sciences (Grant no. DE-FG03-85ER13431). The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094.
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorDespagnet-Ayoub, Emmanuelleen
dc.contributor.authorMiqueu, Karinneen
dc.contributor.authorSotiropoulos, Jean-Marcen
dc.contributor.authorHenling, Lawrence M.en
dc.contributor.authorDay, Michael W.en
dc.contributor.authorLabinger, Jay A.en
dc.contributor.authorBercaw, John E.en
dc.date.accessioned2016-02-28T06:43:27Zen
dc.date.available2016-02-28T06:43:27Zen
dc.date.issued2013en
dc.identifier.citationDespagnet-Ayoub E, Miqueu K, Sotiropoulos J-M, Henling LM, Day MW, et al. (2013) Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene. Chem Sci 4: 2117. Available: http://dx.doi.org/10.1039/c3sc22171g.en
dc.identifier.issn2041-6520en
dc.identifier.issn2041-6539en
dc.identifier.doi10.1039/c3sc22171gen
dc.identifier.urihttp://hdl.handle.net/10754/600135en
dc.description.abstractStarting from the same ethylenediamine species, three valuable carbene precursors were synthesized under differing conditions: a tridentate dianionic N-heterocyclic carbene bearing an aniline, a phenol and a central dihydroimidazolium salt, its benzimidazolium isomer by intramolecular rearrangement and a dicationic benzimidazolium-benzoxazolium salt by changing the Brønsted acid from HCl to HBF4. A DFT study was performed to understand the rearrangement pathway. The structure of a bis[(NCO)carbene] zirconium complex was determined. © 2013 The Royal Society of Chemistry.en
dc.description.sponsorshipThis work was supported by a KAUST Center-In-Development Grant to King Fahd University of Petroleum and Minerals (Dhahran, Saudi Arabia) and the USDOE Office of Basic Energy Sciences (Grant no. DE-FG03-85ER13431). The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleUnexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbeneen
dc.typeArticleen
dc.identifier.journalChemical Scienceen
dc.contributor.institutionCNRS Centre National de la Recherche Scientifique, Paris, Franceen
dc.contributor.institutionUniversite de Toulouse, Toulouse, Franceen
dc.contributor.institutionUniversite de Pau et des Pays de L'Adour, Pau, Franceen
dc.contributor.institutionCalifornia Institute of Technology, Pasadena, United Statesen
All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.