Jon Tunge

Academic Degrees

• B.S. 1995 University of Idaho
• Ph.D., 2000, Columbia University
• Postdoctoral Associate, 2000-02, University of Wisconsin-Madison

Areas of Specialization

Organic Chemistry

Research Interests

Decarboxylative Metalation Reactions in Organic Synthesis. We are establishing a program based on the catalytic generation of reactive organometallic species through decarboxylation. The loss of gaseous CO2 provides a thermodynamic driving force that allows the formation of reactive intermediates under exceptionally mild conditions. Based on this premise, we have recently developed an asymmetric decarboxylative allylation reaction as well as decarboxylative olefin insertion. In these reactions, reactive enolates are regiospecifically formed under non-basic conditions.

Combinatorial Synthesis through Catalytic Hydroarylation. The functionalization of C-H bonds is a major goal in synthetic chemistry. We are interested in the use of C-H functionalization for the combinatorial synthesis of a diverse array of heterocyclic structures. Furthermore, we are interested in studying the mechanisms of C-H functionalizations since it is my belief that understanding how these reactions take place will allow us to new catalysts for the activation and functionalization of C-H bonds.

Selected publications

Li, K.; Tunge, J. A. “Stereochemical Control in the Reduction of 2-Chromanols” Org. Lett.2006, 8, 4711-4714.

Wang, C.; Tunge, J. A. “Decarboxylative Ring Contractions and Olefin Insertions of Vinyl Oxazinanones” Org. Lett. 2006, 8, 3211-3214.

Burger, E., C.; Tunge, J. A. “Synthesis of Homoallylic Amines via the Palladium-catalyzed Decarboxylative Coupling of Amino Acids” J. Am. Chem. Soc. 2006128, 10002-10003.

Waetzig, S. R.; Rayabarapu, D. K.; Weaver, J. D.; Tunge, J. A. “ A Versatile Hexadiene Synthesis via Decarboxylative sp 3-sp 3 Coupling/Cope Rearrangement” Angew. Chem. Int. Ed. 2006, 45, 4977-4980.

Mellegaard-Waetzig, S. R.; Wang, C.; Tunge, J. A. “Selenium-catalyzed Oxidative Halogenation” Tetrahedron2006, 62, 7191-7198.

Rayabarapu, D. K.; Tunge, J. A. “Catalytic Decarboxylative sp-sp 3 Coupling” J. Am. Chem. Soc. 2005, 127, 13510-13511.

Burger, E. C.; Tunge, J. A. “ Asymmetric Allylic Alkylation of Ketone Enolates: An Asymmetric Claisen Surrogate” Org. Lett.2004, 6, 4113-4115.