Dirhodium(II) carboxamidates as oxidation catalysts

ORGN 271

Arthur J. Catino, acatino@umd.edu, Jason M. Nichols, jnicholz@umd.edu, Darren Bykowski, dbykowsk@mail.umd.edu, and Michael P. Doyle, mdoyle3@umd.edu. Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742
Dirhodium(II) caprolactamate [Rh2(cap)4] catalyzes the allylic oxidation of enones and enediones with only 0.1 – 1.0 mol% catalyst loading in combination with tert-butyl hydroperoxide as an oxidant. The effectiveness of Rh2(cap)4 is attributed to its low one-electron oxidation potential and facile redox chemistry (Rh24+/Rh25+). Mechanistic studies aimed at understanding the role of the catalyst will be discussed. In addition, new applications such as benzylic oxidation and enamide oxidation will be highlighted.

 

Metal-Mediated Reactions and Syntheses
1:00 PM-5:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- 202B, Oral

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005