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Joseph O'Connor
Organotransition metal; organic; physical organic; bioorganometallic; synthetic; and inorganic chemistry
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| Contact Information |
| Office: PACH 5100A |
| Phone: (858) 534-5836 |
| Fax: (858) 534-5383 |
| Email: jmoconno@ucsd.edu |
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| Education and Appointments |
| 1984 |
Ph.D., University of Wisconsin, Madison
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| 1979 |
M.S., St. Louis University
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| 1976 |
B.S., John Carroll University
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| Awards and Academic Honors |
| 1991-1994 |
American Cancer Society Junior Faculty Research Fellow |
| 1984-1985 |
Postdoctoral Research Associate, University of California, Berkeley |
| Research Interests |
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.
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| Primary Research Area: |
Interdisciplinary Specialties: |
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Organic Chemistry
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Synthesis
Physical Organic
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| Image Gallery: |
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Figure 1: An eta-4-enediyne complex may be a key intermediate in the metal-catalyzed cycloaromatization of enediynes. Here is shown the crystallographically determined structure of a model ruthenium complex |
Figure 2: The solid-state structure of the first hexahapto dienyne complex |
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Figure 3: The electrostatic potential map calculated for a cobaltacyclobutene complex
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| Selected Publications |
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"Sulfoxide Carbon-Sulfur Bond Activation". With K.D. Bunker, A.L. Rheingold, L. Zakharov. J. Am. Chem. Soc. 2005, 127, 4180-4181.
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"An eta-6-Dienyne Transition-Metal Complex . With S.J. Friese, B.L. Rodgers, A.L. Rheingold, L. Sakharov. J. Am. Chem. Soc. 2005, 127, 9346-9347.
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"A Transition-Metal-Catalyzed Enediyne Cycloaromatization". With S.J. Friese, B.L. Rodgers. J. Am. Chem. Soc. 2005, 127, 16342-16343.
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"Nucleophilic Addition to a p-Benzyne Derived from an Enediyne: A New Mechanism for Halide Incorporation into Biomolecules". With C.L. Perrin, B.L. Rodgers. J. Am. Chem. Soc. 2007, 129, 4795-4799.
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"Reactions of a Metallacyclobutene Complex with Alkenes". With R.L. Holland, K.D. Bunker, C.H. Chen, A.G. DiPasquale, A.L. Rheingold, and K.K. Baldridge. J. Am. Chem. Soc., 2008, 130, 10093-10095.
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"Iridium(III)-vinylidene Chemistry: Conversion of an Iridacyclopentadiene-chlorido Complex and Terminal Alkynes to Iridacyclopentadiene-vinyl Complexes". With A. G. Wenzel and K. Hiibner. Inorg. Chim. Acta 2008, 3033-3041 (Invited manuscript for issue honoring Prof. Robert Angelici).
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"Transition-Metal Hydrides as Hydrogen Atom Donors: Stronger Metal-Hydrogen Bonds Can Be Adventageous". With S. J. Friese. Organometallics 2008, 27, 4280-4281.
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"Nitroso Compounds Serve as Precursors to Late-Metal Hydroxylamido Complexes". WIth R. L. Holland. Organometallics 2009, 28, 394-396
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