Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual ‘dimerization’

Abstract

An unusual ‘dimerization’ of CF3-allyl alcohols [ArCH@CHCH(OH)CF3] under the action of anhydrous FeCl3 was found to give fluorinated indanes in 62–90% yields via the formation of intermediate allyl cations. Reactions of CF3-allyl alcohols with arenes (Ar0H) led to CF3-alkenes in 48–75% yields. The mechanisms of the transformations are discussed.