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      Thermally regulated molybdate-based ionic liquids toward molecular oxygen activation for one-pot oxidative cascade catalysis

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          Abstract

          A family of thermally regulated molybdate-based ionic liquids has been developed for highly efficient synthesis of various flavones, imines, and benzyl benzoates through one-pot oxidative cascade catalysis.

          Abstract

          One-pot oxidative cascade catalysis plays a central role in the synthesis of key pharmaceutical and industrial molecules. Although ionic liquids are one of the most promising solvents and reaction media, the breakthrough of their catalysis in aerobic oxidation is very challenging due to the difficulty in the direct activation of molecular oxygen. Herein, a family of novel thermally regulated molybdate-based ionic liquids (Mo-ILs) has been designed and developed for the first time toward molecular oxygen activation for highly efficient tandem oxidative catalysis. Three diverse one-pot oxidative cascade processes for the syntheses of various flavones, imines, and benzyl benzoates were achieved with good to excellent yields using the Mo-IL [Bmim] 2[MoO 4] as a catalyst under air conditions. The results of spectroscopic investigations and quantum-chemical calculations further demonstrated that a thermally regulated proton migration between the cation [Bmim] and anion [MoO 4] was the key to forming N-heterocyclic carbene and thereby to effortlessly promoting the generation of ˙O 2 active species from molecular oxygen, which results in excellent catalytic performance in these three aerobic tandem oxidations. Our work extends the application area of ILs as the sole catalyst to one-pot aerobic oxidative cascade catalysis, which could have pronounced implications in future work.

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          Author and article information

          Contributors
          Journal
          GRCHFJ
          Green Chemistry
          Green Chem.
          Royal Society of Chemistry (RSC)
          1463-9262
          1463-9270
          January 2 2020
          2020
          : 22
          : 1
          : 103-109
          Affiliations
          [1 ]Key Laboratory of Functional Small Organic Molecule
          [2 ]Ministry of Education
          [3 ]College of Chemistry and Chemical Engineering
          [4 ]Jiangxi Normal University
          [5 ]Nanchang 330022
          Article
          10.1039/C9GC03646F
          © 2020
          Product
          Self URI (article page): http://xlink.rsc.org/?DOI=C9GC03646F

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