Copper-Catalyzed Carboxylation of Hydroborated Disubstituted Alkenes and Terminal Alkynes with Cesium Fluoride

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• 作者：Martin Juhl ; Simon L. R. Laursen ; Yuxing Huang ; Dennis U. Nielsen ; Kim Daasbjerg ; Troels Skrydstrup
• 刊名：ACS Catalysis
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：7
• 期：2
• 页码：1392-1396
• 全文大小：450K
• ISSN：2155-5435

文摘

A protocol for the hydrocarboxylation of disubstituted alkenes and terminal alkynes providing access to different secondary carboxylic acids and malonic acid derivatives has been developed. This methodology relies on an initial hydroboration using 9-BBN followed by carboxylation with carbon dioxide in the presence of a copper catalyst and the additive, cesium fluoride. Different cyclohexene, styrene, and stilbene derivatives could be utilized, and alkynes could be transformed into their corresponding dicarboxylic acids in good yields. Finally, six different terpenoids were carboxylated using the developed procedure.