4.7 Article

DDQ-Mediated Three-Component Dioxygenation of Alkenes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 19, Pages 9350-9355

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01988

Keywords

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Funding

  1. NSFC [21232004, 21272095, 21472071]
  2. PAPD of Jiangsu Higher Education Institutions
  3. Outstanding Youth Fund of JSNU [YQ2015003]
  4. NSF of Jiangsu Province [BK20151163]
  5. Qing Lan Project
  6. NSF of Jiangsu Education Committee [15KJB150006]
  7. Graduate Education Innovation Project of Jiangsu Province [KYZZ15-0385]

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A new DDQ-mediated three-component dioxygenation of alkenes has been established, providing a direct and metal-free access toward densely functionalized 4,5-dichloro-3-hydroxyphthalonitrile derivatives with generally good to excellent yields under mild conditions. During this process, DDQ plays dual roles as both a dehydrogenation reagent and a coupling partner, enabling oxidative coupling to form two C-O functionalities in a highly atom-economy fashion.

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