4.3 Article

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

Journal

BULLETIN OF THE KOREAN CHEMICAL SOCIETY
Volume 32, Issue 10, Pages 3655-3659

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.5012/bkcs.2011.32.10.3655

Keywords

Solid-phase synthesis; Traceless cleavage; Parallel synthesis; Unfunctionalized arenes; Sulfonate linker

Funding

  1. National Research Foundation of Korea (NRF)
  2. Ministry of Education, Science and Technology [2010-0011590]
  3. National Research Foundation of Korea [2010-0011590] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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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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