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Updated: May 1, 2026
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Parallel and combinatorial liquid-phase synthesis of alkylbiphenyls using pentaerythritol support
Wang-Kyu Kim1, Jong-Hoon Jang, Hyunjong Jo
1School of Chemical Engineering and Materials Science, Chung-Ang University , 221 Heukseok-dong, Dongjak-gu, Seoul 156-756, Republic of Korea.
Abstract:
Unfunctionalized alkylbiphenyls were fabricated by a parallel and combinatorial synthesis using pentaerythritol as a tetrapodal soluble support for a sulfonate-based traceless multifunctional linker system. Nickel N-heterocyclic carbene-catalyzed reactions of pentaerythritol tetrakis(biphenylsulfonate)s with primary alkylmagnesium bromides generated the alkylbiphenyl derivatives by desulfitative cleavage/cross-coupling of the C-S bond without any "memory" of the attachment on the support. Though the reactions were completed with sufficient yields in 12 h at room temperature, even with only 1.5 equiv of nucleophiles, they still retained the benefits of facile isolation observed in polymer-supported reactions.
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