Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Department of Chemistry, Faculty of Science, Rikkyo University, 3-34-1 Nishi-Ikebukuro, Toshima-ku, Tokyo 171-8501, Japan.
J Am Chem Soc. 2020 Oct 14;142(41):17323-17328. doi: 10.1021/jacs.0c08928. Epub 2020 Oct 6.
We report the phosphine-catalyzed intermolecular carbofluorination of alkynes using acyl fluorides as fluorinating reagents. This reaction promises to be a useful method for the synthesis of highly substituted monofluoroalkene derivatives since acyl fluorides can be easily prepared from the corresponding carboxylic acid derivatives and the reaction proceeds under ambient conditions without the need for a transition-metal catalyst. Experimental and computational studies indicate that a five-coordinate fluorophosphorane is involved as the key intermediate in the fluorination step.
我们报告了使用酰氟作为氟源，通过膦催化炔烃的分子间碳氟化反应。由于酰氟可以很容易地从相应的羧酸衍生物制备得到，并且反应在环境条件下进行，不需要过渡金属催化剂，因此该反应有望成为合成高取代单氟烯烃衍生物的有用方法。实验和计算研究表明，五配位的氟膦是氟化步骤中的关键中间体。
