Propargylic oxidations catalyzed by dirhodium caprolactamate in water: efficient access to alpha,beta-acetylenic ketones.
Dirhodium(II) caprolactamate (1, Rh 2(cap) 4) with 70% w/w aqueous tert-butyl hydroperoxide (T-HYDRO ) is a highly effective catalytic oxidation protocol for the selective C-H oxidation of alkynes to propargylic ketones. The oxidation occurs readily in aqueous solvent under mild conditions with an inexpensive and easily handled oxidant. Alpha,beta-acetylenic carbonyl compounds are formed in up to 80% isolated yield.
McLaughlin
Emily C
EC
Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.
Doyle
Michael P
MP
D000114:Acetylene / Q000737:chemistry*; D002209:Caprolactam / Q000031:analogs & derivatives* / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D014867:Water / Q000737:chemistry
D007659:Ketones; D009942:Organometallic Compounds; D014867:Water; D002209:Caprolactam; D000114:Acetylene