Nickel-Catalyzed Reductive Coupling of Vinyl Triflates and 1,4-Dicyanobenzene to Access Alkenyl Nitriles |
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Authors: | Le-Le Wang Zhong-Xian Li Jun Zhu |
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Affiliation: | College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072 People's Republic of China |
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Abstract: | We report a vinyl cyanation reaction of vinyl triflates and readily available 1,4-dicyanobenzene through a nickel-catalyzed reductive coupling process. The reaction is operated under mild conditions with remarkable functional-group compatibility. Cyclic vinyl triflates with various ring sizes and substituents at different positions all reacted smoothly. The synthetic utility is demonstrated by the derivatization of pharmaceutical and natural compounds, a scale-up synthesis, and various functional group transformations. Preliminary mechanistic studies demonstrate that vinyl triflates are more reactive than 1,4-dicyanobenzene towards the oxidative addition to nickel catalyst. |
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Keywords: | nickel catalysis reductive coupling vinyl cyanation reaction alkenyl nitrile low toxic nitrile source |
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