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Phosphine-Catalyzed Intermolecular Acylfluorination of Alkynes via a P(V) Intermediate
preprintsubmitted on 12.06.2020, 07:58 and posted on 15.06.2020, 08:28 by Hayato Fujimoto, Takuya Kodama, Masahiro Yamanaka, Mamoru Tobisu
We report on 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-coordinated fluorophosphorane is involved as the key intermediate in the fluorination step.