Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench-Stable Precursor (Me<sub>4sub>N)SCF<sub>3sub>

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• 作者：Thomas Scattolin ; Kristina Deckers and Prof. Dr. Franziska Schoenebeck
• 刊名：Angewandte Chemie International Edition
• 出版年：2017
• 出版时间：January 2, 2017
• 年：2017
• 卷：56
• 期：1
• 页码：221-224
• 全文大小：2218K
• ISSN：1521-3773

文摘

Reported herein is the one-pot synthesis of trifluoromethylated amines at room temperature using the bench-stable (Me<sub>4sub>N)SCF<sub>3sub> reagent and AgF. The method is rapid, operationally simple and highly selective. It proceeds via a formal umpolung reaction of the SCF<sub>3sub> with the amine, giving quantitative formation of thiocarbamoyl fluoride intermediates within minutes that can readily be transformed to N-CF<sub>3sub>. The mildness and high functional group tolerance render the method highly attractive for the late-stage introduction of trifluoromethyl groups on amines, as demonstrated herein for a range of pharmaceutically relevant drug molecules.