Platform for Ring-Fluorinated Benzoheterole Derivatives: Palladium-Catalyzed Regioselective 1,1-Difluoroallylation
Takeshi Fujita1, Kazuki Sugiyama1, Shohei Sanada1
1Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba , Tsukuba, Ibaraki 305-8571, Japan.
Abstract:
The synthesis of difluoromethylene-containing heterocycles was achieved via the palladium-catalyzed 1,1-difluoroallylation of heteronucleophiles followed by intramolecular Heck reaction. The allylic substitution of 3-bromo-3,3-difluoropropene was regioselectively accomplished by heteronucleophiles without rearrangement to give the corresponding 1,1-difluoroallylated compounds whose Heck cyclization proceeded in a 5-exo manner to afford ring-difluorinated indolines and dihydrobenzofurans. Their defluorinative allylic substitution further provided 2-fluoroindoles and 2-fluorobenzofurans.
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