Difluorocarbene Addition to Alkenes and Alkynes in Continuous Flow

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• 作者：Pauline Rullière ; Patrick Cyr ; André B. Charette
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：18
• 期：9
• 页码：1988-1991
• 全文大小：326K
• 年卷期：0
• ISSN：1523-7052

文摘

The first in-flow difluorocarbene generation and addition to alkenes and alkynes is reported. The application of continuous flow technology allowed for the controlled generation of difluorocarbene from TMSCFb>3b> and a catalytic quantity of NaI. The in situ generated electrophilic carbene reacts smoothly with a broad range of alkenes and alkynes, allowing the synthesis of the corresponding difluorocyclopropanes and difluorocyclopropenes. The reaction is complete within a 10 min residence time at high reaction concentrations. With a production flow rate of 1 mmol/min, continuous flow chemistry enables scale up of this process in a green, atom-economic, and safe manner.