ABSTRACT
Rather crafty: 1,1-Difluoroallenes bearing an aryl group and a cyclopentene moiety undergo indium(III)-catalyzed Friedel-Crafts-type cyclization with subsequent ring expansion and dehydrogenation to afford fluorinated polycyclic aromatic hydrocarbons in high yields. The introduction of an Ar group was effected by inâ situ halogenation of the intermediary indium species and a subsequent Suzuki-Miyaura reaction.
ABSTRACT
2-Bromo-3,3-difluoroallylic acetates were readily prepared by the reaction of carbonyl compounds with 1-bromo-2,2-difluorovinyllithium, generated from 1,1-dibromo-2,2-difluoroethylene, followed by acetylation. On treatment with butyllithium, the bromoacetates underwent selective 1,2-elimination of lithium acetate to afford mono- and disubstituted 1,1-difluoroallenes in high yields.