Gold(I)-Catalyzed Alkoxyhalogenation of β-Hydroxy-α,α-Difluoroynones


  • This work was supported the European Community (MRTN-CT-2003-505020, MEIF-CT-2006-039270 and MEIF-CT-2006-040558) and the EPSRC (GR/S79268/02). We thank G. Giuffredi and A. Monney for performing selected experiments, and A. L. Thompson of the Oxford Chemical Crystallography Service for X-ray studies.


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Gold standard: AuCl was found to be the only suitable catalyst for the 6-endo-dig ring closure of hydroxylated difluorinated ynones (see scheme), a class of substrates that displays low reactivity owing to the presence of the gem-difluoro group. For the first time, a gold catalyst is used in combination with an electrophilic fluorinating reagent.