Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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)
  • Received : 2011.07.12
  • Accepted : 2011.08.12
  • Published : 2011.10.20
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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.

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