4.8 Article

Ligand-Enabled Pd(II)-Catalyzed C(sp3)-H Lactonization Using Molecular Oxygen as Oxidant

Journal

ORGANIC LETTERS
Volume 22, Issue 10, Pages 3960-3963

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01243

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Funding

  1. NSF under the CCI Center for Selective C-H Functionalization [CCHE-1700982]
  2. Scripps Research Institute
  3. Bristol-Myers Squibb
  4. NIH [1S10OD025208]

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Pd(II)-catalyzed C-H lactonization of o-methyl benzoic acid substrates has been achieved using molecular oxygen as the oxidant. This finding provides a rare example of C-H oxygenation through Pd(II)/Pd(0) catalysis as well as a method to construct biologically important benzolactone scaffolds. The use of a gas mixture of 5% oxygen in nitrogen demonstrated the possibility for its application in pharmaceutical manufacturing.

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