Protonolysis of a ruthenium-carbene bond and applications in olefin metathesis

Benjamin K. Keitz; Jean Bouffard; Guy Bertrand; Robert H. Grubbs

doi:10.1021/ja203070r

Protonolysis of a ruthenium-carbene bond and applications in olefin metathesis

Benjamin K. Keitz, Jean Bouffard, Guy Bertrand, Robert H. Grubbs

Department of Chemistry & Nanoscience

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

92 Scopus citations

Abstract

The synthesis of a ruthenium complex containing an N-heterocylic carbene (NHC) and a mesoionic carbene (MIC) is described wherein addition of a Brønsted acid results in protonolysis of the Ru-MIC bond to generate an extremely active metathesis catalyst. Mechanistic studies implicated a rate-determining protonation step in the generation of the metathesis-active species. The activity of the NHC/MIC catalyst was found to exceed those of current commercial ruthenium catalysts.

Original language	English
Pages (from-to)	8498-8501
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	22
DOIs	https://doi.org/10.1021/ja203070r
State	Published - 8 Jun 2011

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title = "Protonolysis of a ruthenium-carbene bond and applications in olefin metathesis",

abstract = "The synthesis of a ruthenium complex containing an N-heterocylic carbene (NHC) and a mesoionic carbene (MIC) is described wherein addition of a Br{\o}nsted acid results in protonolysis of the Ru-MIC bond to generate an extremely active metathesis catalyst. Mechanistic studies implicated a rate-determining protonation step in the generation of the metathesis-active species. The activity of the NHC/MIC catalyst was found to exceed those of current commercial ruthenium catalysts.",

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year = "2011",

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AU - Keitz, Benjamin K.

AU - Bouffard, Jean

AU - Bertrand, Guy

AU - Grubbs, Robert H.

PY - 2011/6/8

Y1 - 2011/6/8

N2 - The synthesis of a ruthenium complex containing an N-heterocylic carbene (NHC) and a mesoionic carbene (MIC) is described wherein addition of a Brønsted acid results in protonolysis of the Ru-MIC bond to generate an extremely active metathesis catalyst. Mechanistic studies implicated a rate-determining protonation step in the generation of the metathesis-active species. The activity of the NHC/MIC catalyst was found to exceed those of current commercial ruthenium catalysts.

AB - The synthesis of a ruthenium complex containing an N-heterocylic carbene (NHC) and a mesoionic carbene (MIC) is described wherein addition of a Brønsted acid results in protonolysis of the Ru-MIC bond to generate an extremely active metathesis catalyst. Mechanistic studies implicated a rate-determining protonation step in the generation of the metathesis-active species. The activity of the NHC/MIC catalyst was found to exceed those of current commercial ruthenium catalysts.

UR - https://www.scopus.com/pages/publications/79957971890

U2 - 10.1021/ja203070r

DO - 10.1021/ja203070r

M3 - Article

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SP - 8498

EP - 8501

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 22

ER -

Protonolysis of a ruthenium-carbene bond and applications in olefin metathesis

Abstract

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