研究领域

Organic, Inorganic, and Organometallic Chemistry

1) Organic Methods Development. This area of research will focus on manipulating chemical bonds with transition-metal complexes to develop new reactions that are synthetically and industrially useful. Not only is the group investigating new C-X bond coupling reactions (X = C, H, N, O, S), but we are also studying bond-breaking processes and atom transfer reactions as routes to target molecules. Students will learn to carefully design ligands for transition-metal complexes that will predispose the metal center to carry out a desired chemical transformation. In many cases, forcing a metal to adopt an unconventional geometry can lead to unusual reactivity, and we hope to be able to fine-tune such reactivity towards useful transformations. Click here for a PDF file containing detailed information about our development of paramagnetic nickel complexes for use in organic synthesis. 2) Synthetic Inorganic and Organometallic Chemistry. Nowadays, the fields of organic and inorganic chemistry are intimately related. New catalysts must often be prepared under strict anaerobic conditions using traditional inorganic techniques. Additionally, support for a particular mechanism of a metal-mediated organic transformation is facilitated by preparing viable inorganic and organometallic intermediates and testing for their competency. Students will learn how to prepare new "inorganic functional groups" and explore the structures, properties, and reactivities of these new groups. Sometimes, completely new bonding modes of common atoms can be discovered, like this hydride ligand that displays linear bonding between two metal centers. 3) Fluorine Chemistry. Traditional medicinal chemistry was very much based on the use of natural products or closely related derivatives thereof. Because only a handful of naturally occurring organofluorines were (and still are) known to exist, the use of fluorinated compounds was extremely rare in early medicinal chemistry. This situation has changed quite dramatically over the last 20 years. Today, as many as 30-40% of agrichemicals and 20% of pharmaceuticals on the market are estimated to contain fluorine, including three of the top eight drugs sold in 2008. As developmental pipelines for new drugs are predicted to contain an even higher percentage of fluorinated molecules, developing better methods to prepare organofluorines are expected to be paramount to the health industry. Click here and here for representative papers on our efforts to use transition-metals to incorporate fluorine into organic molecules. 4) New electrochemical methods. Here we hope to understand how one-electron redox reactions can be used in developing new synthetic methodolgy (click here and here for examples).

近期论文

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"Manganese-Catalyzed Aerobic Oxytrifluoromethylation of Styrenyl Olefins Using CF3SO2Na as the Trifluoromethyl Source" Yang, Y.; Liu, Yingle; Jiang, Y.; Zhang, Y.; Vicic, D. A. 2015, submitted. "Iron-Catalyzed Electrochemical C-H Perfluoroalkylation of Arenes" Khrizanforov, M.; Strekalova, S.; Khrizanforova, V.; Grinenko, V.; Kholin, K.; Gryaznova, T.; Sinyashin, O.; Xu, L.; Vicic, D. A.; Budnikova, Y. 2015, submitted. "An Unusual Example of Halogen Bonding to Potassium t-Butoxide" Xu, L.; Cramer, R. E.; Vicic, D. A. J. Fluorine Chem. 2015, in press. "Stepwise Conversion of a Platinum Dimethyl Complex to a Perfluorometallacyclobutane Derivative" Xu, L.; Solowey, D. P.; Vicic, D. A. Organometallics 2015, DOI: .10.1021/acs.organomet.5b00045. "Pyridine-directed and Palladium-Catalyzed Electrochemical Phosphonation of a C(sp2)-H Bond" Dudkina, Y. B.; Gryaznova, T. V.; Islamov, D. R.; Kataeva, O. N.; Sinyashin, O. G.; Vicic, D. A.; Budnikova, Y. H. J. Organomet. Chem 2015, 785, 68-71. "Nanoheterogeneous Catalysis in Electrochemically Induced Olefin Perfluoroalkylation" Dudkina, Y. B.; Gryaznova, T. V.; Davydov, N. A.; Mustafina, A. R.; Vicic, D. A.; Budnikova, Y. B. Dalton Transactions, 2015, in press. "Synthetic Utility of Dizinc Reagents Derived from 1,4-Diiodo- and 1,4-Dibromooctafluorobutane" Kaplan, P. T.; Chen, B.; Vicic, D. A. J. Fluorine Chem. 2014, 168, 158-162. "Synthesis and Reactivity of New Aminophenolate Complexes of Nickel" Yu. S.; Wang, H.; Sledziewski, J. E.; Madhira, V. N.; Takahashi, C. G.; Leon, M. K.; Budnikova, Y. H.; Vicic, D. A. Molecules 2014, 19, 13603-13613. *Invited contribution for the "Practical Applications of Metal Complexes" issue. "Transition Metal Catalyzed Difluoromethylation, Difluoromethylenation, and Polydifluoromethylenation" in the Organometallic Fluorine Chemistry issue of Topics of Organometallic Chemistry, Chen, B.; Vicic, D. A. 2014, DOI: 10.1007/3418_2014_87. "Improved Synthesis, Structure, and Reactivity of 1,4-Bis(trimethylsilyl)octafluorobutane" Chen, B.; Vicic, D. A. J. Fluorine Chem. 2014, 167, 139-142. "Mild, Safe, and Versatile Reagents for (CF2)n Transfer and the Construction of Fluoroalkyl-Containing Rings" Kaplan, P. T.; Xu. L.; Chen, B.; McGarry, K. R.; Yu, S.; Wang, H.; Vicic, D. A. Organometallics 2013, 32, 7552-7558. *This article was highlighted in C&E News 2014, 92, 28-29. "Electrochemical Ortho-Functionalization of Phenylpyridine with Perfluorocarboxylic Acids Catalyzed by Palladium in Higher Oxidation States" Dudkina, Y. B.; Mikhaylov, D. Y.; Gryaznova, T. V.; Tufatullin, A. I.; Kataeva, O. N.; Vicic, D. A.; Budnikova, Y. H. Organometallics 2013, 32, 4785-4792. "Organometallic Aspects of Fluoroalkylation Reactions with Copper and Nickel" Wang, H.; Vicic, D. A. Synlett 2013, 24, 1887-1898.* *This article was a "Most Read" paper for the month of September for Synlett. "A Five-Coordinate Nickel(II) Fluoroalkyl Complex as a Precursor to a Spectroscopically Detectable Ni(III) Species" Zhang, C. P.; Wang, H.; Klein, A.; Biewer, C.; Stirnat, K.; Yamaguchi, Y.; Xu, L.; Gomez-Benitez, V.; Vicic, D. A. J. Am. Chem. Soc. 2013, 135, 8141-8144. “Lithium Bromide-Induced Structural Changes in a Nickel Bis-Alkoxide Complex” Ichioka, H. and Vicic, D. A. Acta Chim. Slov. 2013, 60, 190-192. “Oxidative Cleavage of CH3 and CF3 Radicals from BOXAM Nickel Complexes” Klein, A.; Vicic, D. A.; Biewer, C.; Kieltsch, I.; Stirnat, K.; Hamacher, C. Organometallics 2012, 31, 5334-5341. “Synthesis and Structure of a Bis-Trifluoromethylthiolate Complex of Nickel” Zhang, C. P.; Vicic, D. A. J. Fluorine Chem. 2012, 140, 112-115. “Oxidative Trifluoromethylthiolations of Aryl Boronic Acids Using a Copper/O2 -Based Protocol” Zhang, C. P.; Vicic, D. A. Chem. Asian J. 2012, 7, 1756-1758.* * Highlighted by Angew. Chem. Int. Ed. 2013, 52, 6818-6819 and Eur. J. Org. Chem. 2014, DOI: 10.1002/ejoc.201301857. “Oxygen-Bound Trifluoromethoxide Complexes of Copper and Gold” Zhang, C. P.; Vicic, D. A. Organometallics 2012, 31, 7812-7815.**invited contribution for the "Copper Organometallic Chemistry" issue. This work has also been listed as a "Most Read" (most downloaded) paper for the month of May by the ACS website. “Synthesis and Electronic Properties of a Pentafluoroethyl-Derivatized Nickel Pincer Complex” Madhira, V. N.; Ren, P.; Vechorkin, O.; Hu, X., and Vicic, D. A. Dalton Trans. 2012, 41, 7915-7919.*