4.7 Article

Photoredox-Catalyzed Generation of Sulfamyl Radicals: Sulfonamidation of Enol Silyl Ether with Chlorosulfonamide

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 21, Pages 13897-13907

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02062

Keywords

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Funding

  1. National Science Foundation of China [81573276, 81874287]
  2. Shanghai Biopharmaceutical Science and Technology Supporting Plan [17431902100, 19431900100]
  3. National Science and Technology Major Project Key New Drug Creation and Manufacturing Program, China [2018ZX09711002-003-014]
  4. Fudan-SIMM Joint Research Fund [FU-SIMM20174007]

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A novel and practical photoredox-catalyzed generation of sulfamyl radicals followed by radical sulfonamidation of enol silyl ether has been described. Diverse functionalized beta-ketosulfonamides were prepared in modest to excellent yields under mild and economic reaction conditions through the present catalytic protocol. Furthermore, the methodology developed provides an efficient and convenient approach to the synthesis of the antiseizure drug Zonisamide.

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