title: Palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls.
abstract: The palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols with aryl halides proceeds not only via C-H bond cleavage at the ortho-position, but also via cleavage of the sp(2)-sp(3) C-C bond with the liberation of ketones (beta-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C-C or C-H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. Thus, various biaryls having ortho-substituents can be produced efficiently by treatment of the corresponding aryl(diphenyl or dimethyl)methanols with aryl bromides and chlorides.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
authors.forename: Yoshito
authors.initials: Y
authors.lastname: Terao
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Wakui
authors.forename: Michiyo
authors.initials: M
authors.lastname: Nomoto
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Satoh
authors.forename: Masahiro
authors.initials: M
authors.lastname: Miura
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Nomura