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

doi:10.1039/c3sc22171g

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

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

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 language	English (US)
Pages (from-to)	2117
Journal	Chemical Science
Volume	4
Issue number	5
DOIs	https://doi.org/10.1039/c3sc22171g
State	Published - 2013
Externally published	Yes

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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title = "Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene",

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 Br{\o}nsted 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. {\textcopyright} 2013 The Royal Society of Chemistry.",

author = "Emmanuelle Despagnet-Ayoub and Karinne Miqueu and Jean-Marc Sotiropoulos and Henling, {Lawrence M.} and Day, {Michael W.} and Labinger, {Jay A.} and Bercaw, {John E.}",

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.",

year = "2013",

doi = "10.1039/c3sc22171g",

language = "English (US)",

volume = "4",

pages = "2117",

journal = "Chemical Science",

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publisher = "Royal Society of Chemistry",

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T1 - Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene

AU - Despagnet-Ayoub, Emmanuelle

AU - Miqueu, Karinne

AU - Sotiropoulos, Jean-Marc

AU - Henling, Lawrence M.

AU - Day, Michael W.

AU - Labinger, Jay A.

AU - Bercaw, John E.

N1 - 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.

PY - 2013

Y1 - 2013

N2 - 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.

AB - 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.

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DO - 10.1039/c3sc22171g

M3 - Article

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VL - 4

SP - 2117

JO - Chemical Science

JF - Chemical Science

IS - 5

ER -

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

Abstract

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