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Palladium‐Catalyzed CH Bond Acetoxylation: An Approach to ortho ‐Substituted Hydroxy[2.2]paracyclophane Derivatives
Author(s) -
Lennartz Petra,
Raabe Gerhard,
Bolm Carsten
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200625
Subject(s) - chemistry , palladium , iodobenzene , benzoxazole , catalysis , oxime , pyridine , medicinal chemistry , acetanilide , organic chemistry , combinatorial chemistry
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.