Regioselective C−H Hydroarylation of Internal Alkynes with Arenecarboxylates: Carboxylates as Deciduous Directing Groups
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- 作者：Dr. Liangbin Huang ; Agostino Biafora ; Guodong Zhang ; Valentina Bragoni and Prof. Dr. Lukas J. Gooß ; en
- 刊名：Angewandte Chemie International Edition
- 出版年：2016
- 出版时间：June 6, 2016
- 年：2016
- 卷：55
- 期：24
- 页码：6933-6937
- 全文大小：822K
- ISSN：1521-3773
文摘
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.