Cp₂TiCl₂—Catalyzed Synthesis of Tertiary Alcohols by the Reaction of AlCl₃ with Ketones and Aryl Olefins

Abstract

We have previously obtained significant results in the cycloalumination of olefins with EtAlCl2 in the presence of magnesium and a Cp2ZrCl2 or Cp2TiCl2 catalyst. Here we report the development of an efficient one-pot catalytic method for the synthesis of tertiary alcohols from AlCl3, aryl olefins, and ketones under the action of Cp2TiCl2. The developed method for producing tertiary alcohols has a general character and allows the conversion of styrene and substituted styrenes (ortho-, para-methylstyrenes) into aryl-substituted tertiary alcohols with yields of up to 76% in the reaction with acetone or methyl ethyl ketone. We assume that the reaction proceeds through the formation of a titanacyclopropane intermediate.

Keywords

• titanocene
• catalysis
• arylolefines
• ketones
• tertiary alcohols