Pd-catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants under mild conditions: A dual role for carboxylic anhydrides in catalytic C-H bond oxidation

Ramesh Giri, Jue Liang, Jian Guang Lei, Jiao Jie Li, Dong Hui Wang, Xiao Chen, Isaac Clement Naggar, Chengyun Guo, Bruce M. Foxman, Jin Quan Yu

Research output: Contribution to journalArticlepeer-review

336 Scopus citations

Abstract

(Chemical Equation Presented) Unactivated CH3 groups in 2-oxazolines are oxidized by inexpensive oxidants, such as tert-butyl peroxyacetate and lauroyl peroxide, in the presence of a catalytic amount of Pd(OAc)2. Carboxylic anhydrides are essential for both the oxidation of the Pd-C bonds and regeneration of Pd(OAc)2. The use of [D 6]Ac2O as the solvent shows that the acetyl group incorporated into the product is from acetic anhydride rather than the oxidant (see scheme).

Original languageEnglish (US)
Pages (from-to)7420-7424
Number of pages5
JournalAngewandte Chemie - International Edition
Volume44
Issue number45
DOIs
StatePublished - Dec 1 2005

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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