Isolation and Interconversion of Protic N-Heterocyclic Carbene and Imidazolyl Complexes: Application to Catalytic Dehydrative Condensation of N-(2-Pyridyl)benzimidazole and Allyl Alcohol

Kenjirou Araki,Takao Ikariya,Shigeki Kuwata

doi:10.1021/om800285n

Isolation and Interconversion of Protic N-Heterocyclic Carbene and Imidazolyl Complexes: Application to Catalytic Dehydrative Condensation of N-(2-Pyridyl)benzimidazole and Allyl Alcohol

Kenjirou Araki, Takao Ikariya + Show 1 more

https://doi.org/10.1021/om800285n

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Journal: Organometallics	Publication Date: Apr 19, 2008
Citations: 123

Affiliation: Tokyo Institute of Technology

#N-heterocyclic Carbene Complex #Bifunctional Complex + Show 8 more

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Abstract

Treatment of the protic N-heterocyclic carbene (NHC) complex [Cp*RuCl(LH)] (2; LH = N-(2-pyridyl)benzimidazolin-2-ylidene-κ2N,C) with AgNO2 gives the nitrosyl–imidazolyl complex [Cp*Ru(NO)(L)][OTf] (OTf = OSO2CF3), which undergoes reversible protonation to afford the NHC complex [Cp*Ru(NO)(LH)][OTf]2. The bifunctional complex 2 also catalyzes the dehydrative condensation of N-(2-pyridyl)benzimidazole and allyl alcohol, leading to the formation of trans- and cis-2-(1-propenyl)-N-(2-pyridyl)benzimidazole.

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