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Phosphine-Catalyzed Intermolecular Acylfluorination of Alkynes via a P(V) Intermediate

preprint
submitted on 12.06.2020 and posted on 15.06.2020 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.

Funding

JSPS KAKENHI 18H01978

JSPS KAKENHI Hybrid Catalysis 20H04818

History

Email Address of Submitting Author

tobisu@chem.eng.osaka-u.ac.jp

Institution

Osaka University

Country

Japan

ORCID For Submitting Author

0000-0002-8415-2225

Declaration of Conflict of Interest

No conflict of interest

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