TY - JOUR A1 - Fujita, Takeshi A1 - Kinoshita, Ryo A1 - Takanohashi, Tsuyoshi A1 - Suzuki, Naoto A1 - Ichikawa, Junji T1 - Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes JF - Beilstein Journal of Organic Chemistry PY - 2017/// VL - 13 SP - 2682 EP - 2689 SN - 1860-5397 DO - 10.3762/bjoc.13.266 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.13.266 KW - alkenes KW - carbocycles KW - cyclization KW - electrophilic activation KW - fluorine KW - iodine N2 - 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. ER -