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Vanadium-Catalyzed Coupling of Allenols with Electrophilic Halide Sources for the Formation of α-Halo-α',β'-unsaturated Ketones

Barry M. Trost*, Jacob S. Tracy, Tas Yusoontorn

*Department of Chemistry, Stanford University, 333 Campus Drive, Stanford, California 94305, United States, Email: bmtroststanford.edu

B. M. Trost, J. S. Tracy, T. Yusoontorn, Org. Lett., 2019, 21, 1207-1211.

DOI: 10.1021/acs.orglett.9b00195 (free Supporting Information)



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Abstract

A vanadium-catalyzed coupling of allenylic alcohols with electrophilic halide sources provides α-halo-α',β'-unsaturated ketones. Fluorine, chlorine, and bromine electrophiles can be utilized, and the resulting products can give rise to the introduction of nitrogen, oxygen, sulfur, and iodine nucleophiles α to the ketone through substitution chemistry.


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Key Words

enones, fluorination, NFSI


ID: J54-Y2019