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1,1-Difluoro-1-alkenes bearing a biaryl-2-yl group effectively underwent site-selective intramolecular iodoarylation by the appropriate cationic iodine species. Iodoarylation of 2-(2-aryl-3,3-difluoroallyl)biaryls proceeded via regioselective carbon–carbon bond formation at the carbon atoms in β-position to the fluorine substituents, thereby constructing dibenzo-fused six-membered carbocycles bearing a difluoroiodomethyl group. In contrast, 2-(3,3-difluoroallyl)biaryls underwent a similar cyclization at the α-carbon atoms to afford ring-difluorinated seven-membered carbocycles.

A Versatile Difluorovinylation Method: Cross-Coupling Reactions of the 2,2-Difluorovinylzinc-TMEDA Complex with Alkenyl, Alkynyl, Allyl, and Benzyl Halides. -Title zinc complex (II) is synthesized and applied to transition metal-catalyzed cross-coupling reactions with a wide range of organic halides yielding 2,2-difluorovinyl compounds. Complex (II) is storable and can easily be handled. -(ICHITSUKA, T.; TAKANOHASHI, T.; FUJITA, T.; ICHIKAWA*, J.; J. Fluorine Chem. 170 (2015) 29-37, http://dx.