Phosphine-Catalyzed Intermolecular Acylfluorination of Alkynes via a P(V) Intermediate
Phosphine-Catalyzed Intermolecular Acylfluorination of Alkynes via a P(V) Intermediate
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DOI：
10.1021/jacs.0c08928
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发表时间：
2020-10-14
影响因子：
15
通讯作者：
Tobisu, Mamoru
中科院分区：
文献类型：
--
作者：
Fujimoto, Hayato;Kodama, Takuya;Tobisu, Mamoru
本文报道了以酰氟为氟化试剂，膦催化的炔的分子间羰基化反应。该反应有望成为合成高度取代的单氟烯烃衍生物的有用方法，因为酰氟可以容易地由相应的羧酸衍生物制备，并且反应在环境条件下进行而不需要过渡金属催化剂。实验和计算研究表明，五配位的氟磷烷参与的关键中间体在催化步骤。
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.