Journal of the American Chemical Society · 2014 · 94 citations · 49 references
Chemical EngineeringCross-coupling ReactionEngineeringAlkene MetathesisCatalytic SynthesisBorylated FuransOrganic ChemistryFormal 1,2-Hydrogen ShiftOrganometallic CatalysisCatalysisHomogeneous CatalysisChemistrySynthesis MethodSynthetic ChemistryC3-borylated FuransGold Catalyst
A regioselective transition metal-catalyzed cycloisomerization reaction of boron-containing alkynyl epoxides toward C2- and C3-borylated furans has been developed. It was found that the copper catalyst as well as the gold catalyst with more basic triflate counterion favor boryl migration toward C3-borylated furans, whereas employment of the cationic gold hexafluoroantimonate affords C2-borylated furan via a formal 1,2-hydrogen shift.
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Alexander S. Dudnik, Anna W. Sromek, Marina Rubina et al. · Journal of the American Chemical Society · 2008 · 305 citations · Full text