Palladium‐Catalyzed CH Bond Acetoxylation: An Approach to

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Abstract:

Abstract

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

Document Type: Research Article

DOI: http://dx.doi.org/10.1002/adsc.201200625

Affiliations: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: (+49)-241-809-2391

Publication date: November 26, 2012

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