Award Address (Elias J. Corey Award for Outstanding Original Contribution in Organic Synthesis by a Young Investigator, sponsored by The Pfizer Endowment Fund). Formation of C-C bonds via catalytic hydrogenation

ORGN 346

Michael J Krische, mkrische@mail.utexas.edu, Department of Chemistry and Biochemistry, University of Texas at Austin, Mail Code A5300, Austin, TX 78712
Hydrogenation ranks among the most powerful catalytic methods employed industrially, accounting for over half the chiral compounds made by man not produced via physical or enzymatic resolution. This fact portends an equally powerful approach to reductive C-C bond formations mediated by hydrogen – catalytic couplings achieved simply through the exposure of two or more molecules to gaseous hydrogen in the presence of a metallic catalyst. Whereas classical methods for the addition of C-nucleophiles to carbonyl compounds generally require stoichiometric preformation of moisture sensitive organometallics, “C-C bond forming hydrogenation” enables direct coupling of diverse p-unsaturated reactants under neutral conditions with complete atom economy. In this account, we describe the discovery and development of the first hydrogen-mediated C-C couplings beyond alkene hydroformylation, transformations that add a new dimension to one of chemistry's oldest and most broadly utilized processes.