Organic Letters
Organic Letters
4 years ago

Co-Catalyzed Cross-Coupling Reaction of Alkyl Fluorides with Alkyl Grignard Reagents

Co-Catalyzed Cross-Coupling Reaction of Alkyl Fluorides with Alkyl Grignard Reagents
Nobuaki Kambe, Takanori Iwasaki, Koji Yamashita, Hitoshi Kuniyasu
The cross-coupling reaction of unactivated alkyl fluorides with alkyl Grignard reagents by a CoCl2/LiI/1,3-pentadiene catalytic system is described. The present reaction smoothly cleaved C–F bonds under mild conditions and achieved alkyl–alkyl cross-coupling even when sterically hindered tertiary alkyl Grignard reagents were employed. Since alkyl fluorides are inert toward many reagents and catalytic intermediates, the use of the present reaction enables a new multistep synthetic route to construct carbon frameworks by combining conventional transformations.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01370

DOI: 10.1021/acs.orglett.7b01370

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