Traceless liquid-phase synthesis of biphenyls and terphenyls using pentaerythritol as a tetrapodal soluble support.
Application of a novel sulfonate-based traceless multifunctional linker system using pentaerythritol as a tetrapodal soluble support was demonstrated using liquid-phase parallel and combinatorial preparation of biphenyl and terphenyl compounds. Nickel-catalyzed reactions of pentaerythritol tetrakis(arenesulfonate)s with arylmagnesium bromides generated the desired products in sufficient yields through reductive cleavage/cross-coupling of the C-S bond. Homogeneous pentaerythritol-supported reactions could be accomplished using less nucleophile with shorter reaction periods than could the corresponding heterogeneous polymer-supported reactions. This liquid-phase approach using a small polyfunctionalized support combines advantages of solution-phase and solid-phase syntheses by allowing high reactivity, high atom economy, simple isolation, and real-time monitoring of the reaction progress.
Kim
Chul-Bae
CB
School of Chemical Engineering and Materials Science, Chung-Ang University, 221 Heukseok-Dong, Dongjak-Gu, Seoul 156-756, South Korea..
Cho
Chul-Hee
CH
Kim
Chang Keun
CK
Park
Kwangyong
K
D001713:Biphenyl Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D002849:Chromatography, Gas; D020650:Combinatorial Chemistry Techniques; D003432:Cross-Linking Reagents / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D008956:Models, Chemical; D009532:Nickel / Q000737:chemistry; D011409:Propylene Glycols / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013730:Terphenyl Compounds / Q000138:chemical synthesis*
D001713:Biphenyl Compounds; D003432:Cross-Linking Reagents; D006842:Hydrocarbons, Brominated; D009532:Nickel; D011409:Propylene Glycols; D013438:Sulfhydryl Compounds; D013730:Terphenyl Compounds; C010574:biphenyl; C008783:pentaerythritol