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      Interrupted Fischer-indole intermediates via oxyarylation of alkenyl boronic acids.

      1 ,
      Organic letters
      American Chemical Society (ACS)

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          Abstract

          The oxyarylation of alkenyl boronic acids with N-arylbenzhydroxamic acids has been achieved under both copper-mediated and copper-catalyzed conditions to provide access to interrupted Fischer-indole intermediates. This transformation is believed to proceed through a copper-promoted C-O bond forming event followed by a [3,3] rearrangement. The scope of the method is described and mechanistic experiments are discussed.

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          Author and article information

          Journal
          Org. Lett.
          Organic letters
          American Chemical Society (ACS)
          1523-7052
          1523-7052
          Jul 05 2013
          : 15
          : 13
          Affiliations
          [1 ] Department of Chemistry, University of Illinois, Chicago, Illinois 60607, USA.
          Article
          10.1021/ol401416r
          23799801
          c434cdce-3089-48d8-8b48-f11e84960785
          History

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