Pd(II)-catalyzed o-C-H acetoxylation of phenylalanine and ephedrine derivatives with MeCOOO(t)Bu/Ac2O

Org Lett. 2010 Jun 4;12(11):2511-3. doi: 10.1021/ol1007108.

Abstract

Pd(II)-catalyzed ortho C-H acetoxylation of triflate protected phenethyl- and phenpropylamines has been achieved with tert-butyl peroxyacetate as the stoichiometric oxidant and either DMF or CH(3)CN as the promoter. The reaction was found to tolerate a large variety of functional groups and could be combined with subsequent intramolecular amination to afford functionalized indoline derivatives.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amination
  • Catalysis
  • Ephedrine / analogs & derivatives*
  • Ephedrine / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Palladium / chemistry*
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemistry*

Substances

  • Indoles
  • Phenylalanine
  • Palladium
  • indoline
  • Ephedrine