Nickel-Catalyzed Cross-Electrophile Coupling of Alkyl Fluorides: Stereospecific Synthesis of Vinylcyclopropanes

Lucas W. Erickson, Erika L. Lucas, Emily J. Tollefson, Elizabeth R. Jarvo

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44 Scopus citations

Abstract

The stereospecific reductive cross-electrophile coupling reaction of 2-vinyl-4-halotetrahydropyrans for vinylcyclopropane synthesis is reported. The nickel-catalyzed reaction occurs with both alkyl fluorides and alkyl chlorides. To the best of our knowledge, this is the first reported cross-electrophile coupling reaction of an alkyl fluoride. Ring contraction proceeds with high stereospecificity, providing selective synthesis of either diastereomer of di- and trisubstituted cyclopropanes. The utility of this methodology is demonstrated by several synthetic applications including the synthesis of the natural product dictyopterene A. 2-Vinyl-4-fluorotetrahydrofurans also undergo stereospecific ring contractions, providing access to synthetically useful hydroxymethyl cyclopropanes.

Original languageEnglish (US)
Pages (from-to)14006-14011
Number of pages6
JournalJournal of the American Chemical Society
Volume138
Issue number42
DOIs
StatePublished - Oct 26 2016

Bibliographical note

Publisher Copyright:
© 2016 American Chemical Society.

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