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

Despagnet-Ayoub, Emmanuelle and Miqueu, Karinne and Sotiropoulos, Jean-Marc and Henling, Lawrence M. and Day, Michael W. and Labinger, Jay A. and Bercaw, John E. (2013) Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene. Chemical Science, 4 (5). pp. 2117-2121. ISSN 2041-6520 . http://resolver.caltech.edu/CaltechAUTHORS:20130507-074545359

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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 HBF_4. A DFT study was performed to understand the rearrangement pathway. The structure of a bis[(NCO)carbene] zirconium complex was determined.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1039/c3sc22171g DOIArticle
http://pubs.rsc.org/en/Content/ArticleLanding/2013/SC/c3sc22171gPublisherArticle
ORCID:
AuthorORCID
Despagnet-Ayoub, Emmanuelle0000-0002-9013-7574
Labinger, Jay A.0000-0002-1942-9232
Additional Information:© 2013 The Royal Society of Chemistry. Received 7th December 2012. Accepted 25th February 2013. First published online 26 Feb 2013. 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.
Funders:
Funding AgencyGrant Number
King Abdullah University of Science and Technology (KAUST)UNSPECIFIED
Department of Energy (DOE)DE-FG03-85ER13431
NSFCHE-0639094
Record Number:CaltechAUTHORS:20130507-074545359
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20130507-074545359
Official Citation:Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene Emmanuelle Despagnet-Ayoub, Karinne Miqueu, Jean-Marc Sotiropoulos, Lawrence M. Henling, Michael W. Day, Jay A. Labinger and John E. Bercaw Chem. Sci., 2013, 4, 2117-2121 DOI: 10.1039/C3SC22171G
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:38306
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:07 May 2013 15:33
Last Modified:16 Nov 2017 21:20

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