Palladium‐Catalyzed CH Bond Acetoxylation: An Approach to ortho‐Substituted Hydroxy[2.2]paracyclophane Derivatives

作者: Petra Lennartz , Gerhard Raabe , Carsten Bolm

DOI: 10.1002/ADSC.201200625

关键词: Medicinal chemistryOximeCatalysisOrganic chemistryPyrazoleChemistryPlanar chiralityIodobenzenePalladiumPyridineBenzoxazole

摘要: The palladium-catalyzed direct CH bond acetoxylation of [2.2]paracyclophanes has been investigated. Various mono- and disubstituted were subjected to typical Sanford conditions. Oxime ethers, an oxime acetate, a pyridine, pyrazole with [2.2]paracyclophane cores underwent ortho-acetoxylation in good excellent yields using 1–5 mol% palladium(II) acetate combination iodobenzene diacetate as oxidant. reactions could be performed on multigram scale, the ortho-acetoxylated suitable for further functionalizations affording hydroxy[2.2]paracyclophane derivative planar chiral benzoxazole.

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