(Research Description PDF - 870 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.
C–H Activation/Borylation/Oxidation: A One-Pot Unified Route to Meta-Substituted Phelols Bearing Ortho-/Para-Directing Groups, R. E. Maleczka Jr., F. Shi, D. Holmes, M.R. Smith III, J. Am. Chem. Soc. 2003, 125, 7792.
Remarkably Selective Iridium Catalysts for Elaboration of C–H Bonds, J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka Jr., M. R. Smith III, Science 2002, 295, 305.
Steric and Chelate Directing Effects in Aromatic Borylation, J.-Y. Cho, C. N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 2001, 123,12868.
Stereoselective Polymerization of a Racemic Monomer with a Racemic Catalyst: Direct Preparation of the Polylactic Acid Stereocomplex from Racemic Lactide, C. P. Radano, G. L. Baker, M. R. Smith III, J. Am. Chem. Soc. 2000, 122, 1552.
Stoichiometric and Catalytic B–C Bond Formation from Unactivated Hydrocarbons and Boranes, C. N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 1999, 121, 7696.
B.S., 1986, California Institute of Technology
Ph.D., 1990, Univ. of Chicago
Postdoctoral Fellow, 1990-92, Univ. of California, Berkeley.
|Award||Organization||Division||Level Code||Type Code||Start Date||End Date|
|Merck Technology Symposium's Technology Collaboration Award||Professional||Honors||2013|
|Distinguished Service in Boron Science Award||Professional||Honors||2008|
|Presidential Green Chemistry Challenge Award||Professional||Honors||2008|
|Postdoctoral Fellow||University California, Berkeley||Postdoctoral||Fellowship||1990||1992|
|Ph.D.||University of Chicago||Graduate||Degree||1990|
|Bachelor of Science||California Institute of Technology||Undergraduate||Degree||1986|
Jason Unold received the Department of Physiology's Undergraduate Research Award for his studies on catalytic borylations carried out in the Maleczka and Smith labs.
On Thursday September 12 at noon in BPS 1400 Prof. Smith will discuss the possibility of using liquid ammonia as a renewable hydrogen carrier and outline the problems associated this approach.
Professors Mitch Smith and Rob Maleczka along with their collaborators Drs. Shane Krska and Peter Maligres recently received the 2013 Merck Technology Symposium's Technology Collaboration Award for their work on high throughput optimization of Ir-catalyzed C-H borylations. Sean Preshlock and Behnaz Ghaffari were among the MSU students who participated in the award winning work.
Amy Pochodylo's poster entitled "EFFECT OF ALIPHATIC DICARBOXYLATE TETHER ON TOPOLOGY IN LUMINESCENT CADMIUM COORDINATION POLYMERS CONTAINING BIS (4- PYRIDYLFORMYL) PIPERAZINE" earned a best poster award at the 2012 University Undergraduate Research & Arts Forum. Amy is a Lyman Briggs Chemistry major working with Professor Rob La Duca. Approximately 560 undergraduate students participated in this year’s UURAF, including Jake Ludwig (Tepe lab), Fangyi Shen (Maleczka lab) and Hongtu Zhang (Smith lab).
Damith Perera's poster entitled “Cross-Couplings that Avoid the Preparation of Haloaromatics: The Development of a One- Pot C–H Activation/Borylation/Suzuki Reaction with Immidazolylsulfonates as the Electrophilic Partner” earned second place honors in the poster competition held at Green Up the 3rd Michigan Green Chemistry Conference. This conference took place in Ann Arbor on October 27. Damith's poster was co-authored by Professors Mitch Smith and Rob Maleczka, as well as Jennifer Albaneze-Walker, Process Research and Development, Merck Inc., Rahway NJ.
Britt Vanchura won the Journal of Chemical Crystallography Prize for his poster at the American Crystallographic Association annual meeting last week in Toronto. His poster is on the 4th floor outside Mitch Smith's office, along with the nice rosette he received at the banquet.
At the Boron in the America's XI Conference held June 4-8th in St. Louis, Professor Mitch Smith received the Distinguished Service in Boron Science Award, Professor Mitch Smith and Professor Robert Maleczka were awarded the Presidential Green Chemistry Challenge Award, as was SiGNa Chemistry, a company cofounded by Jim Dye with ongoing participation by Ned Jackson's research group. At the same conference Venkata A. Kallepalli won 1st place for the best oral presentation by a graduate student. Lastly, Michigan State University was announced as the host of Boron in the America's XII, which will occur in 2010. More
Rob Maleczka and Mitch Smith have received a $100,000 grant from the Pharmaceutical Roundtable of the Green Chemistry Institute, a division of the American Chemical Society. The grant will be used to further their work that can be used to promote green engineering practices in the pharmaceutical industry. More
Rob Maleczka and Mitch Smith received $1.38M, one of the 61 awards from the State of Michigan 2006 21st Century Jobs Fund. The title of their proposal was "Catalytic Boronate Ester Synthesis: Developing New Commercial Building Blocks for Drug Discovery."