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James Stambuli received his B.A. degree from Rutgers University in 1998, and his Ph.D. in 2003 from Yale University working with Professor John F. Hartwig. He was a National Institutes of Health Postdoctoral Fellow in the laboratories of Professor Barry M. Trost at Stanford University before joining The Ohio State University as an Assistant Professor in 2006.
Metal-catalyzed Reactions, Carbon-Carbon and Carbon-Heteroatom Bonds, Reaction Principles
Research in our group is directed toward the development of new methods for organic synthesis. We will focus on designing metal-catalyzed reactions that construct carbon-carbon and carbon-heteroatom bonds. Method development will be complemented with mechanistic studies to outline basic reaction principles and accelerate catalyst discovery.
C-H Activation Reactions. A major directive of our research group is the development of C-H activation reactions. Recently, we discovered the use of novel thioether ligands in the allylic oxidation of terminal olefins. Mechanistic studies of this process along with the synthesis of novel thioether ligands are currently underway.
Calcium-Catalyzed Reactions. The use of calcium catalysts in organic synthesis is an underdeveloped area of research. We are currently preparing novel calcium complexes and studying their reactivity in Pictet-Spengler and hydroamination reactions that form nitrogen heterocycles. Additional Lewis acid-catalyzed reactions employing these complexes are currently being investigated.
Synthesis of Oxazoles. Our group has developed a nickel-catalyzed cross coupling reaction of alkylthio-oxazoles and organozinc reagents to form the corresponding substituted oxazoles. This reaction is currently being employed in the synthesis of natural products and pharmaceuticals that contain oxazole moieties. Additional strategies toward the synthesis of oxazoles are also currently being investigated.
Synthesis of Late Metal Sulfoxide and Thiolate Complexes. Our group is also involved in the synthesis of novel late metal complexes ligated by mono- and bidentate sulfoxide ligands. The activation of small molecules using these complexes is currently being investigated.
Henderson, W. H.; Check, C. T.; Proust, N.; Stambuli, J. P. Allylic Oxidations of Terminal Olefins Using a Palladium Thioether Catalyst. Org. Lett., 2010, 12, 824.
Eichman, C. C.; Stambuli, J. P. Zinc-Mediated Palladium-Catalyzed Formation of Carbon Sulfur Bonds. J. Org. Chem. 2009, 74, 4005.
Lee, K.; Counceller, C. M.; Stambuli, J. P. Nickel-Catalyzed Synthesis of Oxazoles via C-S Activation. Org. Lett. 2009, 11, 1457.
Vanden Eynden, M. J.; Stambuli, J. P. Calcium-Catalyzed Pictet-Spengler Reactions. Org. Lett. 2008, 10, 5289-5291. (reviewed in ACS “Noteworthy Chemistry” on 12/1/2008)
Counceller, C. M.; Eichman, C. C.; Wray, B. C.; Stambuli, J. P. A Practical, Metal-Free Synthesis of 1H-Indazoles. Org. Lett. 2008, 10, 1021-1023. (reviewed in Synfacts 2008, 6, 580)