4.7 Article

Copper-Catalyzed One-Pot Synthesis of Unsymmetrical Arylurea Derivatives via Tandem Reaction of Diaryliodonium Salts with N-Arylcyanamide

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 17, Pages 8156-8162

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo501334u

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Funding

  1. Minjiang Scholar Program [10BS216]
  2. Xiamen Southern Oceanographic Center [13GYY003NF16]
  3. Natural Science Foundation of Fujian Province, China [2013J01050]
  4. Fundamental Research Funds of Huaqiao University

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An efficient one-pot approach to multiple substituted ureas from N-arylcyanamide and diaryliodonium salts has been presented. The two-step procedure involved the weak base-promoted chemoselective arylation of secondary amines with diaryliodonium and Cu-catalyzed nucleophilic addition of N-arylcyanamide with second diaryliodonium. The diverse unsymmetrical arylureas were obtained in up to 91% yield for 29 examples.

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