TCDA: Practical Synthesis and Application in the Trifluoromethylation of Arenes and Heteroarenes

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• 作者：Jian Wang ; Xiaomin Zhang ; Zehong Wan ; Feng Ren
• 刊名：Organic Process Research & Development
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：20
• 期：4
• 页码：836-839
• 全文大小：264K
• 年卷期：0
• ISSN：1520-586X

文摘

A practical synthesis of the reagent trimethylsilyl chlorodifluoroacetate (TCDA) is reported on 50 g scale. The trifluoromethylation with TCDA was optimized, and the reaction shows very broad scope with respect to electron-deficient, -neutral, -rich aryl/heteroaryl iodides, as well as excellent functional group tolerability, such as ester, amide, aldehyde, hydroxyl, and carboxylic acid. The reagent was also applied to the late-stage trifluoromethylation of three medicinally relevant compounds. Additionally, the building block trifluoromethylpyridine and one drug related molecule Boc-Fluoxetin were synthesized in 10 g scale by this method, demonstrating its practical applications in process chemistry.