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submitted on 12.06.2020 and posted on 15.06.2020by 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.