个人简介

B.S., 1986, California Institute of Technology Ph.D., 1990, Univ. of Chicago Postdoctoral Fellow, 1990-92, Univ. of California, Berkeley. AwardOrganizationDivisionLevel CodeType CodeStart DateEnd Date Merck Technology Symposium's Technology Collaboration AwardProfessionalHonors2013 Distinguished Service in Boron Science AwardProfessionalHonors2008 Presidential Green Chemistry Challenge AwardProfessionalHonors2008 Postdoctoral FellowUniversity California, BerkeleyPostdoctoralFellowship19901992 Ph.D.University of ChicagoGraduateDegree1990 Bachelor of ScienceCalifornia Institute of TechnologyUndergraduateDegree1986

研究领域

Biological Inorganic Materials Organometallic

(Research Description PDF - 1148 kb) Inventing chemical reactions for new syntheses using organometallic complexes and the design of new biodegradable polymers based on polylactic acids is the focus of our research. In addition to basic training in synthesis and polymer chemistry, students in my group develop expertise in the gamut of modern analytical methods for molecular and macromolecular characterization and are exposed to a broad range of science through extensive collaborations with other groups on campus. Overviews of two current projects are given below. The first project involves transition metal chemistry of boron. We began our research in this area with hopes of exploring the fundamental chemistry of metal boryl complexes (M–BX2) and examining reactions of boron-element bonds with unsaturated organic ligands coordinated to metal centers. In the course of this work, we discovered unusual selectivities for olefin borylation reactions and were able to control catalytic chemistry by tuning the ligands attached to boron. Most recently, we reported the first example of catalytic synthesis of a B–C bond from an arene C–H bond and a borane B–H bond. This marked a significant advance in catalytic hydrocarbon functionalization, which has been one of chemistry’s “Holy Grails”. In addition, the sterically dictated regioselectivities in these reactions provide the first general solutions to long-standing problems in aromatic substitution chemistry. In the future, we plan to explore issues that dictate selectivity in these reactions. The second research area involves the synthesis of biodegradable and biorenewable polymers through ring-opening polymerization reactions. These are important materials that provide environmentally friendly alternatives to petroleum-based polymers. We presently are designing polylactic acid copolymers that can be tailored for applications in tissue regeneration and drug delivery. This project has spawned a collaboration studying bone growth with the Department of Physiology.

近期论文

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"Outer-Sphere Direction in Iridium C–H Borylation" Roosen, P. C., Kallepalli, V. A., Chattopadhyay, B., Singleton, D. A., Maleczka, R. E., Jr. and Smith, M. R., III J. Am. Chem. Soc. 2012, 134, 11350-11353. "Practical One-Pot C-H Activation/Borylation/Oxidation: Preparation of 3-Bromo-5-methylphenol on a Multigram Scale" Norberg, A. M., Smith, M. R., III and Maleczka, R. E., Jr. Synthesis-Stuttgart 2011, 857-859. "Electronic effects in iridium C-H borylations: insights from unencumbered substrates and variation of boryl ligand substituents" Vanchura, B. A., Preshlock, S. M., Roosen, P. C., Kallepalli, V. A., Staples, R. J., Maleczka, R. E., Jr., Singleton, D. A. and Smith, M. R., III Chem. Commun. 2010, 46, 7724-7726. "Divergent Synthesis of 2,3,5-Substituted Thiophenes by C-H Activation/Borylation/Suzuki Coupling" Kallepalli, V. A., Sanchez, L., Li, H., Gesmundo, N. J., Turton, C. L., Maleczka, R. E., Jr. and Smith, M. R., III Heterocycles 2010, 80, 1429-1448. "Boc Groups as Protectors and Directors for Ir-Catalyzed C-H Borylation of Heterocycles" Kallepalli, V. A., Shi, F., Paul, S., Onyeozili, E. N., Maleczka, R. E., Jr. and Smith, M. R., III J. Org. Chem. 2009, 74, 9199-9201. "Getting the sterics just right: a five-coordinate iridium trisboryl complex that reacts with C-H bonds at room temperature" Chotana, G. A., Vanchura, B. A., Tse, M. K., Staples, R. J., Maleczka, R. E., Jr. and Smith, M. R., III Chem. Commun. 2009, 5731-5733. "Water-soluble thermoresponsive polylactides" Jiang, X. W., Smith, M. R., III and Baker, G. L. Macromolecules 2008, 41, 318-324. ""Clickable" polyglycolides: Tunable synthons for thermoresponsive, degradable polymers" Jiang, X., Vogel, E. B., Smith, M. R., III and Baker, G. L. Macromolecules 2008, 41, 1937-1944. "Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C-H functionalization" Chotana, G. A., Kallepalli, V. A., Maleczka, R. E., Jr. and Smith, M. R., III Tetrahedron 2008, 64, 6103-6114. "Glass transitions in polylactides" Baker, G. L., Vogel, E. B. and Smith, M. R., III Polymer Reviews 2008, 48, 64-84. "Synthesis of polymandelide: A degradable polylactide derivative with polystyrene-like properties" Liu, T. Q., Simmons, T. L., Bohnsack, D. A., Mackay, M. E., Smith, M. R., III and Baker, G. L. Macromolecules 2007, 40, 6040-6047. "Cyclohexyl-substituted polyglycolides with high glass transition temperatures" Jing, F., Smith, M. R., III and Baker, G. L. Macromolecules 2007, 40, 9304-9312. "Amphiphilic PEG/alkyl-grafted comb polylactides" Jiang, X. W., Vogel, E. B., Smith, M. R., III and Baker, G. L. Journal of Polymer Science Part a-Polymer Chemistry 2007, 45, 5227-5236. "Aromatic borylation/amidation/oxidation: A rapid route to 5-substituted 3-amidophenols" Shi, F., Smith, M. R., III and Maleczka, R. E., Jr. Org. Lett. 2006, 8, 1411-1414. "Regulation of osteoblast gene expression and phenotype by polylactide-fatty acid surfaces" Porter, K., Hossain, M., Wang, M., Radano, C. P., Baker, G., Smith, M. R., III and McCabe, L. R. Molecular Biology Reports 2006, 33, 1-12. "Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: Nitrogen-directed aromatic borylation" Paul, S., Chotana, G. A., Holmes, D., Reichle, R. C., Maleczka, R. E., Jr. and Smith, M. R., III J. Am. Chem. Soc. 2006, 128, 15552-15553. "One-pot borylation/amination reactions: Syntheses of arylamine boronate esters from halogenated arenes" Holmes, D., Chotana, G. A., Maleczka, R. E., Jr. and Smith, M. R., III Org. Lett. 2006, 8, 1407-1410. "Synthesis and polymerization of derivatized lactide monomers" Vogeley, N. J., Baker, G. L. and Smith, M. R., III Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) 2005, 46, 336. "Sterically Directed Functionalization of Aromatic C-H Bonds: Selective Borylation Ortho to Cyano Groups in Arenes and Heterocycles" Chotana, G. A., Rak, M. A. and Smith, M. R., III J. Am. Chem. Soc. 2005, 127, 10539-10544. "Functionalizing polylactides for tissue growth" Wang, M., Radano, C. P., Mackay, M. E., McCabe, L. R., Baker, G. L. and Smith, M. R., III Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) 2003, 44, 716. "C-H activation/borylation/oxidation: A one-pot unified route to meta-substituted phenois bearing ortho-/para-directing groups" Maleczka, R. E., Jr., Shi, F., Holmes, D. and Smith, M. R., III J. Am. Chem. Soc. 2003, 125, 7792-7793. "Synthesis of novel biodegradable copolymers using olefin metathesis" Radano, C. P., Baker, G. L. and Smith, M. R., III Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) 2002, 43, 727-728. "Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds" Cho, J. Y., Tse, M. K., Holmes, D., Maleczka, R. E., Jr. and Smith, M. R., III Science 2002, 295, 305-308.