4.7 Article

Palladium-Catalyzed Intermolecular Oxidative Cyclization of Allyltosylamides with AcOH: Assembly of 3-Pyrrolin-2-ones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 15, Pages 8191-8198

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00804

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Funding

  1. National Key Research and Development Program of China [2016YFA0602900]
  2. National Natural Science Foundation of China [21420102003]
  3. Fundamental Research Funds for the Central Universities [2015ZY001]

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The first example of Pd-catalyzed oxidative cyclization of allyltosylamides with acetic acid is reported. This transformation involved C-N/C-C bond formation and provided 3-pyrrolin-2-ones in a one-pot manner with easy-operation, excellent atom economy and good yields. Mechanistic studies indicate that the reaction proceeds through intermolecular aminopalladation, migratory insertion, reinsertion and beta-hydride elimination processes.

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