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http://dx.doi.org/10.5012/bkcs.2011.32.10.3655

Solid-Phase Synthesis of Unfunctionalized Arenes Via the Traceless Cleavage of Sulfonate Linkers  

Kim, Chul-Bae (School of Chemical Engineering and Materials Science, Chung-Ang University)
Cho, Chul-Hee (School of Chemical Engineering and Materials Science, Chung-Ang University)
Jo, Min-Jy (School of Chemical Engineering and Materials Science, Chung-Ang University)
Park, Kwang-Yong (School of Chemical Engineering and Materials Science, Chung-Ang University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.10, 2011 , pp. 3655-3659 More about this Journal
Abstract
The hydrogenolysis of polymer-bound arenesulfonates by 2-propylmagnesium chloride was performed through reductive cleavage of the C-S bond in the presence of a nickel catalyst. The reaction underwent in the highest efficiency by adding 15 equiv of the nucleophile in two additions with $dppfNiCl_2$ in THF. Various unfunctionalized naphthalene, biphenyl, and stilbene derivatives were produced in good yields by the traceless sulfonate linker system at room temperature.
Keywords
Solid-phase synthesis; Traceless cleavage; Parallel synthesis; Unfunctionalized arenes; Sulfonate linker;
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