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Synlett 1997; 1997(5): 606-608
DOI: 10.1055/s-1997-3228
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Facile Preparation of Fluorine-containing Alkenes, Amides and Alcohols via the Electrophilic Fluorination of Alkenyl Boronic Acids and Trifluoroborates

Nicos A. Petasis* , Andrei K. Yudin, Ilia A. Zavialov, G. K. Surya Prakash1 , George A. Olah1
  • *Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661
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Publication History

Publication Date:
31 December 2000 (online)

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Reaction of alkenyl boronic acids, or preferably alkenyl trifluoroborates, with one equivalent of SelectfluorTM gives the corresponding alkenyl fluorides. A similar reaction with two equivalents of SelectfluorTM in water or a nitrile solvent gives difluoromethyl-substituted alcohols and amides respectively.

alkenyl boronic acid - trifluoroborate - selectfluor - alkenyl fluoride difluoromethyl alcohol - difluoromethyl amide - fluoro-Ritter reaction