Palladium‐Catalyzed CH Bond Acetoxylation: An Approach to
Authors: Lennartz, Petra; Raabe, Gerhard; Bolm, Carsten
Source: Advanced Synthesis & Catalysis, Volume 354, Number 17, 26 November 2012 , pp. 3237-3249(13)
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
Affiliations: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: (+49)-241-809-2391
Publication date: 2012-11-26