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Stereospecific Ni-Catalyzed Cross-Coupling of Potassium Alkenyltrifluoroborates with Alkyl Halides

Gary A. Molander* and O. Andreea Argintaru

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States, Email: gmolandrsas.upenn.edu

G. A. Molander, O. A. Argintaru, Org. Lett., 2014, 16, 1904-1907.

DOI: 10.1021/ol500408a (free Supporting Information)



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Abstract

An alkenylation of alkyl electrophiles using nearly stoichiometric amounts of air- and moisture-stable potassium organotrifluoroborates tolerates various functional groups on both the nucleophilic and electrophilic partner. Reactions of highly substituted E- and Z-alkenyltrifluoroborates, as well as vinyl- and propenyltrifluoroborates, were successful with retention of stereochemistry and regiochemistry.

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Key Words

alkenes


ID: J54-Y2014