A highly
efficient and regioselective annulation of benzodiynes
promoted by triflic acid has been developed. This protocol provides
a step and atom-economic access to a series of naphthalenyl triflates.
Furthermore, direct synthetic applications of this reaction are also
elaborated through cross-coupling reactions to generate synthetically
useful multisubstituted naphthalenes.
The synthesis of gem-difluoroethylene compounds remains a difficult task in organic synthesis. Here, the direct difluoroethylation reactions of N- and O-nucleophiles including amides and acids were realized with a hypervalent iodine reagent: gem-difluorovinyl iodonium salt (DFVI). The reactions were accomplished via a neighbouring group rearrangement. The gem-difluorovinyl iodonium salt was found to display diverse reactivity due to its unique electronic effect and was applied to the incorporation of difluoroethylene group, including difluorovinylation of carboxylic acids, difluorovinylation and 1,3-cyclic fluorovinylation of amides and 1,1-cyclic difluoroethylation of amines.
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