Palladium-Catalyzed Ring-Opening/Defluorinative Annulation of gem-Difluorocyclopropanes With β-Keto Sulfones:
Wanqing Lu1, Ge Liang1, Juanjuan Wu2
1Key Laboratory of Advanced Light Conversion Materials and Biophotonics, School of Chemistry and Life Resources, Renmin University of China, Beijing, China.
Abstract:
A concise and efficient route to the synthesis of multi-substituted furans has been developed via Pd-catalyzed ring-opening/defluorinative annulation of gem-difluorocyclopropanes (gem-F2CPs) with β-keto sulfones. Control experiments indicated that the reaction proceeds through a linear rather than a branched fluoroalkene intermediate, and further incorporates the C2 and C3 atoms of the gem-F2CP motif into the furan skeletons selectively. Besides, the synthetic utility of this protocol was demonstrated through the modification of bioactive molecules and transformations of furan products into 1,4-epoxynaphthalene derivatives.
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