Cationic Rhodium(I) Tetrafluoroborate Catalyzed Intramolecular Carbofluorination of Alkenes via Acyl Fluoride C−F Bond Activation**

Author:

Yoshida Tomoki1,Ohta Masaya1,Emmei Tomoya1,Kodama Takuya12,Tobisu Mamoru12ORCID

Affiliation:

1. Department of Applied Chemistry Graduate School of Engineering Osaka University Suita Osaka 565-0871 Japan

2. Innovative Catalysis Science Division Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI) Osaka University Suita Osaka 565-0871 Japan

Abstract

AbstractThe C−F bond of acyl fluorides can be cleaved and added across tethered alkenes in the presence of a cationic rhodium(I) tetrafluoroborate catalyst. This 1,2‐carbofluorination reaction offers a powerful method for the synthesis of tertiary alkyl fluoride derivatives with an atom economy of 100 %. Mechanistic studies indicate that the concerted action of a rhodium cation and a tetrafluoroborate anion is key for the success of this catalytic cleavage and formation of C−F bonds in a controlled manner.

Funder

Japan Society for the Promotion of Science

Publisher

Wiley

Subject

General Medicine

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