2012 University of California San Diego Distinguished Teaching Award 2011 Fellow, American Association for the Advancement of Science 1991-1994 American Cancer Society Junior Faculty Research Fellow 1986, 1987 UC Chancellor's Faculty Fellowship 1984-1985 Postdoctoral Research Associate, University of California, Berkeley

Organic Chemistry

Radically new transformations of inorganic and organic molecules are highly desirable due to the impact that chemical reactivity has on diverse areas of the chemical sciences, such as pharmaceuticals, specialty chemicals, catalysis, materials, theory, etc. Highlighted below are three representative areas of ongoing research in the O'Connor group, which afford students opportunities to become experts in synthetic and mechanistic chemistry.Bioorganometallic Chemistry. Bioorganometallic chemistry is only now in its infancy; however, it is clear that a great deal of exciting chemistry lies at the interface of biology and organometallic chemistry. We are currently developing new organometallic triggering mechanisms and technology for drug delivery. An example invovles the synthesis of new organometallic DNA cleavage agents in which a metal is employed to stabilize highly reactive organic enediyne molecules, deliver the molecules to biological targets (e.g. DNA), and ultimately to provide for new triggering mechanisms for unmasking the desired biological activity. In related work, new metal-catalyzed Bergman cycloaromatization of enediynes and Hopf cycloaromatization of dienynes is leading to the development of new metal-catalyzed synthetic methodology.Metallacyclobutene Chemistry. Metallacyclobutenes have been proposed as key intermediates in numerous metal-catalyzed reactions of alkynes and cyclopropenes, yet little is known about the chemistry of late-metal metallacyclobutenes. We have developed a new route into metallacyclobutene complexes based on the reactions of metal-alkyne complexes with diazocarbonyls. This new chemistry has opened the door to the first broad-based reactivity studies on late-metal metallacyclobutenes. Early results indicate that this class of compounds represents useful and exciting new reactive intermediates for chemical synthesis.Carbon-Sulfur Bond Activation. Carbon-element bond activation by transition metals is one of the most challenging areas of modern chemical research. Our first direct observation of metal insertion into a sulfoxide carbon-sulfur bond has now set the stage for a new chapter in carbon-element bond activation. We are now examining the scope, limitations, and mechanism of this fundamentally new bond activation process.

Baldridge, K. K.; Bunker, K. D.; Velez, C. L.; Holland, R. L.; Rheingold, A. L.; Moore, C. E.; O'Connor, J. M. "Structural Characterization of (C5H5)Co(PPh3)(η2-alkyne) and (C5H5)Co(η2-alkyne) Complexes of Highly Polarized Alkynes", Organometallics, 2013, Vol. 32, in press Bunker, K. D.; Rheingold, A. L.; Moore, C. E.; Aubrey, M.; O'Connor, J. M. "Synthesis of the Cobalt-Alkyne Complex (η5-C5H5)(PPh3)Co{η2-(Me3Si)C≡C(CO2Et)} and Structural Characterization of Trimethylsilyl Substituted Cobaltacyclopentadiene Complexes Derived Therefrom", J. Organomet. Chem., 2013, in press O’Connor, J. M.; Baldridge, K. K.; Vélez, C. L.; Rheingold, A. L.; Moore, C. E. "Chemistry at the Alkyne – Carbene Intersection: A Metallacyclobutene – η3-Vinylcarbene Equilibration", J. Am. Chem. Soc., 2013, Vol. 135, 8826 Hitt, D. M.; O'Connor, J. M. "Acceleration of Conjugated Dienyne Cycloaromatization", Chem. Rev., 2011, Vol. 111, 7876 O'Connor, J. M.; Chen, M.-C.; Holland, R. L.; Rheingold, A. L. "Addition of Dissimilar Carbenes Across an Unsymmetrically Substituted Alkyne: Regio- and Stereoselective Synthesis of Trisubstituted 1,3-Dienes", Organometallics, 2011, Vol. 30, 369 O’Connor, J. M.; Baldridge, K. K.; Rodgers, B. L.; Aubrey, M.; Holland, R. L.; Kassel, W. S.; Rheingold, A. L. "A Photochemical Metallocene Route to Anionic Enediynes: Synthesis, Solid-state Structures, and ab Initio Computations on Cyclopentadienidoenediynes", J. Am. Chem. Soc., 2010, Vol. 132, 11030 Vélez, C. L.; Markwick, P. R. L.; Holland, R. L.; DiPasquale, A.; Rheingold, A. L.; O’Connor, J. M. "Cobalt 1,3-Diisopropyl-1H-imidazol-2-ylidene Complexes: Synthesis, Solid-state Structures, and Quantum Chemistry Calculations", Organometallics, 2010, Vol. 29, 6695 Holland, R. L.; Bunker, K. D.; Chen, C. H.; DiPasquale, A. G.; Rheingold, A. L.; Baldridge, K. K.; O’Connor, J. M. "Reactions of a Metallacyclobutene Complex with Alkenes", J. Am. Chem. Soc., 2008, Vol. 130, 10093 Perrin, C. L.; Rodgers, B. L.; O'Connor, J. M. "Nucleophilic Addition to a p-Benzyne Derived from an Enediyne: A New Mechanism for Halide Incorporation into Biomolecules", J. Am. Chem. Soc., 2007, Vol. 129, 4795