Ruthenium Induced C-N Bond Activation of an N-Heterocyclic Carbene: Isolation of C- and N-Bound Tautomers

Suzanne Burling; Mary F Mahon; Rachael E Powell; Michael K Whittlesey; Jonathan M J Williams

doi:10.1021/ja065582k

Ruthenium Induced C-N Bond Activation of an N-Heterocyclic Carbene: Isolation of C- and N-Bound Tautomers

Suzanne Burling, Mary F Mahon, Rachael E Powell, Michael K Whittlesey, Jonathan M J Williams

Department of Chemistry

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

167 Citations (SciVal)

Abstract

C-N bond activation of the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene occurs with Ru(PPh3)3(CO)HCl to give the C-2 bound 1-isopropyl-4,5-dimethylimidazol-2-ylidene complex Ru(C-IiPrHMe2)(PPh3)2(CO)HCl via loss of propene. In the presence of free carbene, this undergoes tautomerism to the corresponding imidazole compd. Ru(N-IiPrHMe2)(PPh3)2(CO)HCl. The crystal structures of both carbon and nitrogen bound tautomers is described.

Original language	English
Pages (from-to)	13702-13703
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	42
DOIs	https://doi.org/10.1021/ja065582k
Publication status	Published - 2006

Keywords

heterocyclic carbene tautomer ruthenium imidazolylidene prepn crystal mol structure
Tautomers (isolation and structural characterization of carbon- and nitrogen-bound tautomers prepd. via ruthenium induced carbon-nitrogen bond activation of N-heterocyclic carbene)
ruthenium carbon nitrogen bond activation
Bond (carbon-nitrogen activation
Crystal structure
isolation and structural characterization of carbon- and nitrogen-bound tautomers prepd. via ruthenium induced carbon-nitrogen bond activation of N-heterocyclic carbene)
isopropyl dimethyl imidazolylidene reaction ruthenium carbonyl phosphine hydride
PREP (Preparation) (isolation and structural characterization of carbon- and nitrogen-bound tautomers prepd. via ruthenium induced carbon-nitrogen bond activation of N-heterocyclic c
PRP (Properties)
Carbene complexes Role
Molecular structure (of carbon- and nitrogen-bound tautomers of ruthenium induced carbon-nitrogen bond activation of N-heterocyclic carbene)
SPN (Synthetic preparation)

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10.1021/ja065582k

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title = "Ruthenium Induced C-N Bond Activation of an N-Heterocyclic Carbene: Isolation of C- and N-Bound Tautomers",

abstract = "C-N bond activation of the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene occurs with Ru(PPh3)3(CO)HCl to give the C-2 bound 1-isopropyl-4,5-dimethylimidazol-2-ylidene complex Ru(C-IiPrHMe2)(PPh3)2(CO)HCl via loss of propene. In the presence of free carbene, this undergoes tautomerism to the corresponding imidazole compd. Ru(N-IiPrHMe2)(PPh3)2(CO)HCl. The crystal structures of both carbon and nitrogen bound tautomers is described.",

keywords = "heterocyclic carbene tautomer ruthenium imidazolylidene prepn crystal mol structure, Tautomers (isolation and structural characterization of carbon- and nitrogen-bound tautomers prepd. via ruthenium induced carbon-nitrogen bond activation of N-heterocyclic carbene), ruthenium carbon nitrogen bond activation, Bond (carbon-nitrogen activation, Crystal structure, isolation and structural characterization of carbon- and nitrogen-bound tautomers prepd. via ruthenium induced carbon-nitrogen bond activation of N-heterocyclic carbene), isopropyl dimethyl imidazolylidene reaction ruthenium carbonyl phosphine hydride, PREP (Preparation) (isolation and structural characterization of carbon- and nitrogen-bound tautomers prepd. via ruthenium induced carbon-nitrogen bond activation of N-heterocyclic c, PRP (Properties), Carbene complexes Role, Molecular structure (of carbon- and nitrogen-bound tautomers of ruthenium induced carbon-nitrogen bond activation of N-heterocyclic carbene), SPN (Synthetic preparation)",

author = "Suzanne Burling and Mahon, \{Mary F\} and Powell, \{Rachael E\} and Whittlesey, \{Michael K\} and Williams, \{Jonathan M J\}",

year = "2006",

doi = "10.1021/ja065582k",

language = "English",

volume = "128",

pages = "13702--13703",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "42",

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T1 - Ruthenium Induced C-N Bond Activation of an N-Heterocyclic Carbene: Isolation of C- and N-Bound Tautomers

AU - Burling, Suzanne

AU - Mahon, Mary F

AU - Powell, Rachael E

AU - Whittlesey, Michael K

AU - Williams, Jonathan M J

PY - 2006

Y1 - 2006

N2 - C-N bond activation of the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene occurs with Ru(PPh3)3(CO)HCl to give the C-2 bound 1-isopropyl-4,5-dimethylimidazol-2-ylidene complex Ru(C-IiPrHMe2)(PPh3)2(CO)HCl via loss of propene. In the presence of free carbene, this undergoes tautomerism to the corresponding imidazole compd. Ru(N-IiPrHMe2)(PPh3)2(CO)HCl. The crystal structures of both carbon and nitrogen bound tautomers is described.

AB - C-N bond activation of the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene occurs with Ru(PPh3)3(CO)HCl to give the C-2 bound 1-isopropyl-4,5-dimethylimidazol-2-ylidene complex Ru(C-IiPrHMe2)(PPh3)2(CO)HCl via loss of propene. In the presence of free carbene, this undergoes tautomerism to the corresponding imidazole compd. Ru(N-IiPrHMe2)(PPh3)2(CO)HCl. The crystal structures of both carbon and nitrogen bound tautomers is described.

KW - heterocyclic carbene tautomer ruthenium imidazolylidene prepn crystal mol structure

KW - Tautomers (isolation and structural characterization of carbon- and nitrogen-bound tautomers prepd. via ruthenium induced carbon-nitrogen bond activation of N-heterocyclic carbene)

KW - ruthenium carbon nitrogen bond activation

KW - Bond (carbon-nitrogen activation

KW - Crystal structure

KW - isolation and structural characterization of carbon- and nitrogen-bound tautomers prepd. via ruthenium induced carbon-nitrogen bond activation of N-heterocyclic carbene)

KW - isopropyl dimethyl imidazolylidene reaction ruthenium carbonyl phosphine hydride

KW - PREP (Preparation) (isolation and structural characterization of carbon- and nitrogen-bound tautomers prepd. via ruthenium induced carbon-nitrogen bond activation of N-heterocyclic c

KW - PRP (Properties)

KW - Carbene complexes Role

KW - Molecular structure (of carbon- and nitrogen-bound tautomers of ruthenium induced carbon-nitrogen bond activation of N-heterocyclic carbene)

KW - SPN (Synthetic preparation)

UR - https://www.scopus.com/pages/publications/33750293969

U2 - 10.1021/ja065582k

DO - 10.1021/ja065582k

M3 - Article

SN - 0002-7863

VL - 128

SP - 13702

EP - 13703

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 42

ER -

Ruthenium Induced C-N Bond Activation of an N-Heterocyclic Carbene: Isolation of C- and N-Bound Tautomers

Abstract

Keywords

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