4.7 Article

Ru-Catalyzed δ-Arylation of para-Quninone Methides with Aryl Diazonium Salts to Synthesize Fuchsones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 11, Pages 7238-7246

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00621

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Funding

  1. National Natural Science Foundation of China (NSFC) [21571087, 81872647]
  2. Natural Science Foundation of the Jiangsu Higher Education Institutions of China [17KJB150016, 18KJA150004]
  3. TAPP

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A novel reaction mode and efficient ruthenium-catalyzed Matsuda-Heck-type arylation of para-quinone methides (p-QMs) with aryl diazonium salts has been developed for the synthesis of symmetrical or unsymmetrical delta,delta'-diaryl quinone methides (fuchsones). Aryl groups are introduced at the delta-position of p-QMs via tandem olefin insertion reaction/beta-H elimination processes. This reaction features advantages such as mild and green conditions, broad reactant scope, and high yields.

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