title: Trifluoromethanesulfonic acid catalyzed friedel-Crafts alkylations of 1,2,4-trimethoxybenzene with aldehydes or benzylic alcohols.
abstract: Trifluoromethanesulfonic acid in acetonitrile was found to efficiently catalyze Friedel-Crafts alkylations of 1,2,4-trimethoxybenzene with a variety of simple or functionalized aldehydes to provide di- or triarylmethanes in high yields. The operationally simple protocol allowed a short synthesis of the phenylpropanoid natural product (-)-tatarinoid C establishing its absolute configuration. Under the developed reaction conditions a benzylic alcohol instead of an aldehyde also underwent reactions with 1,2,4-trimethoxybenzene and other nucleophiles to afford unsymmetrically substituted compounds.
authors: Institut für Chemie und Biochemie, Freie Universität Berlin , Takustr. 3 14195 Berlin, Germany.
authors: Michael
authors: M
authors: Wilsdorf
authors: Daniel
authors: D
authors: Leichnitz
authors: Hans-Ulrich
authors: HU
authors: Reissig
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000478:Alkylation; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D008698:Mesylates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D001555:Benzene Derivatives; D001593:Benzyl Compounds; D008698:Mesylates; C508108:1,2,4-trimethoxybenzene; C012077:trifluoromethanesulfonic acid