4.7 Article

Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 21, Pages 13465-13472

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01646

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Funding

  1. Guangdong Provincial Key Laboratory of Construction Foundation [2017B030314030]
  2. Guangdong Natural Science Foundation [2015A030313184]
  3. Science and Technology Program of Guangzhou [201607010118]

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Copper-catalyzed difunctionalization of 2-vinyl-benzoic acids with sodium sulfinates to construct substituted lactones has been realized. This protocol employs inexpensive CuCl2 as the catalyst, di-tert-butyl peroxide or O-2 as the terminal oxidant, and readily available sodium sulfinates as sulfonylation reagents. High functional group tolerance and excellent yields were demonstrated by the efficient preparation of a wide range of gamma-sulfonylated phthalides.

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