Regioselective C−H Hydroarylation of Internal Alkynes with Arenecarboxylates: Carboxylates as Deciduous Directing Groups |
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Authors: | Dr Liangbin Huang Agostino Biafora Guodong Zhang Valentina Bragoni Prof?Dr Lukas J Gooßen |
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Institution: | FB Chemie-Organische Chemie, Technische Universit?t Kaiserslautern, Kaiserslautern, Germany |
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Abstract: | In the presence of catalytic Ru(p‐cym)I2]2 and the base guanidine carbonate, benzoic acids react with internal alkynes to give the corresponding 2‐vinylbenzoic acids. This alkyne hydroarylation is generally applicable to diversely substituted electron‐rich and electron‐poor benzoic and acrylic acids. Aryl(alkyl)acetylenes react regioselectively with formation of the alkyl‐branched hydroarylation products, and propargylic alcohols are converted into γ‐alkylidene‐δ‐lactones. The hydroarylation can also be conducted decarboxylatively with a different choice of catalyst and reaction conditions. This reaction variant, which does not proceed via intermediate formation of 2‐vinylbenzoic acids, opens up a regioselective, waste‐minimized synthetic entry to vinylarenes. |
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Keywords: | alkynes C− H activation decarboxylation ruthenium synthetic methods |
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