title: Gold-catalyzed addition of N-hydroxy heterocycles to alkynes and subsequent 3,3-sigmatropic rearrangement.
abstract: Gold-catalyzed intermolecular addition of hydroxybenzotriazole derivatives to alkynes at room temperature, gives vinyl ethers 3 in high yields and with excellent regioselectivity. Unlike many other vinyl ethers, 3 can easily be purified by regular silica-gel chromatography. On heating, 3,3-sigmatropic rearrangement of 3 gives access to highly functionalized benzotriazoles. This two-step sequence represents an efficient oxygen transfer protocol which incorporates a nucleophilic oxygen atom into an alkyne group. Reaction of 3 with an electrophilic fluorinating reagent (Selectfluor) gives a fluorinated ketone regioselectively and in high yield.
authors: Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, United States.
authors: Manish
authors: M
authors: Kumar
authors: Martin
authors: M
authors: Scobie
authors: Mark S
authors: MS
authors: Mashuta
authors: Gerald B
authors: GB
authors: Hammond
authors: Bo
authors: B
authors: Xu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D014230:Triazoles; D014753:Vinyl Compounds; C100195:vinyl ether; D006046:Gold; C012771:benzotriazole