sp3 C-H functionalization via Lewis acid induced intramolecular redox cascades

ORGN 31

Kevin M. McQuaid and Dalibor Sames, sames@chem.columbia.edu. Department of Chemistry, Columbia University, 3000 Broadway, MC3133, New York, NY 10027
Despite recent advances in the field of C-H functionalization, methods transforming sp3 C-H bonds into new C-C bonds remain rare. We have recently developed a general hydroalkylation methodology for a variety of sp3 C-H bonds via a [1,5] hydride transfer/cyclization cascade. This intramolecular-redox strategy requires no stoichiometric oxidants or reagents and is catalyzed by simple Lewis acids. We have also observed significant rate enhancements through the use simple organic molecules as co-catalysts. These strategies will be discussed along with reaction scope and applications in complex organic synthesis.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Rm. R04, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008