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, John E. Bercaw

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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 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.
Original languageEnglish (US)
Pages (from-to)2117
JournalChemical Science
Volume4
Issue number5
DOIs
StatePublished - 2013
Externally publishedYes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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