Atom economic synthesis of amides via transition metal catalyzed rearrangement of oxaziridines

INOR 163

Robert H. Crabtree, robert.crabtree@yale.edu, Yale Chemistry Department, New Haven, CT 06520 and Chin Hin Leung, chinhin.leung@yale.edu, Department of Chemistry, Yale University, 225 Prospect Street, P.O. Box 208107, New Haven, CT 06511.
A mild synthetic route to amides involves imine oxidation to an oxaziridine, followed by rearrangement to the amide. The first step of this route is catalyzed by a relative non-toxic tungsten compound at low catalyst loading, using H2O2 as oxidant, while Ir, Rh and Mn compounds effectively catalyze the second. Traditional synthesis of amide usually produces stoichiometric amounts of waste products. Using transition metal catalysis under mild reaction conditions, this route shows potential as a greener alternative to form amides.
 

Applications of Organometallic Chemistry
7:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Sci-Mix

Division of Inorganic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007