title: Access to "Friedel-Crafts-restricted" tert-alkyl aromatics by activation/methylation of tertiary benzylic alcohols.
abstract: Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl(2) or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.
authors.affiliation: Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, USA.
authors.forename: Joshua A
authors.initials: JA
authors.lastname: Hartsel
authors.forename: Derek T
authors.initials: DT
authors.lastname: Craft
authors.forename: Qiao-Hong
authors.initials: QH
authors.lastname: Chen
authors.forename: Ming
authors.initials: M
authors.lastname: Ma
authors.forename: Paul R
authors.initials: PR
authors.lastname: Carlier
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D001555:Benzene Derivatives; D001593:Benzyl Compounds