4.7 Article

Synthesis of Triarylmethanes by Decarbonylation of 3,3-Diaryl Benzofuranones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 8, Pages 5300-5311

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03433

Keywords

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Funding

  1. Natural Science Foundation of China [21676076, 21878071, 21971060]
  2. Hu-Xiang High Talent in Hunan Province [2018RS3042]
  3. Recruitment Program for Foreign Experts of China [WQ20164300353]

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A simple protocol for the synthesis of triarylmethane derivatives with three different (hetero)aryl groups by decarbonylation of 3,3-diaryl benzofuranones, which can easily be prepared via arylation of benzofuranones, was developed. The reaction proceeds on heating in dimethylformamide (DMF) in the presence of CH3ONa and water to generate the products in good to excellent yields. This reaction can be easily scaled up to give a triarylmethane in a gram scale. Further chemical manipulation of the products enabled useful transformations of the phenol ring, including reduction, arylation, cyclization, etc.

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