Design and synthesis of N-heterocyclic carbenes for organocatalytic redox reactions

ORGN 565

Justin R. Struble and Jeffrey W. Bode, bode@chem.ucsb.edu. Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106-9510
Recently, we have developed a variety of novel C−C and C−O bond forming redox reactions mediated by N-heterocyclic carbene (NHC) organocatalysts. These reactions are atom economical, stereoselective, enantioselective, and operationally friendly. Tuning of the catalysts by structure (imidazolium, triazolium, or thiazolium), steric, or electronic properties can partition a single set of substrates and conditions to completely different reaction outcomes. We will present these results along with new procedures for the synthesis of several classes of chiral and achiral NHC precatalysts.