4.8 Article

Copper-Catalyzed Arylsulfonylation and Cyclizative Carbonation of N-(Arylsulfonyl)acrylamides Involving Desulfonative Arrangement toward Sulfonated Oxindoles

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ORGANIC LETTERS
卷 19, 期 21, 页码 5844-5847

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02827

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资金

  1. National Natural Science Foundation of China [21272028, 21572025, 21602019]
  2. Innovation & Entrepreneurship Talents Introduction Plan of Jiangsu Province
  3. Key University Science Research Project of Jiangsu Province [15KJA150001]
  4. Jiangsu Key Laboratory of Advanced Catalytic Materials Technology [BM2012110]
  5. Advanced Catalysis and Green Manufacturing Collaborative Innovation Center
  6. Young Natural Science Foundation of Jiangsu Province [BK20150263]

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Sulfonated oxindoles are accessed by a Cu(OAc)(2)-catalyzed three-component reaction of N-(arylsulfony1)acrylamides, DABSO, and aryldiazonium tetrafluoroborates. This transformation is triggered by the formation of arylsulfonyl radicals in situ from the reaction of aryldiazonium tetrafluoroborates and DABSO. Afterward, the sequential radical addition, radical cyclization, and desulfonylative 1,4-aryl migration take place to provide the final product by the formation of four new bonds in one pot. This procedure shows good functional group tolerance.

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