Additional Departments/Affiliated Programs::
Prof. Zajc obtained the PhD degree from the University of Ljubljana, Slovenia, and did postdoctoral work as a Fogarty Fellow at the National Institutes of Health, Bethesda. She moved from University of Ljubljana, where she was a tenured faculty member, to The City College of New York, where she is currently a tenured Associate Professor.
B.Sc. University of Ljubljana, Slovenia
M.Sc. University of Ljubljana, Slovenia
PhD University of Ljubljana, Slovenia
Prof. Zajc’s research is in the area of organofluorine chemistry, with the focus on development of novel regiospecific fluorination methods, and the use of fluorine as a probe in studies related to metabolism and biological activity of environmental pollutants. The importance for this area of research is exemplified in the fact that over 150 commercial pharmaceuticals contain fluorine atom.
In the area of methods development, novel fluorinated building blocks are synthesized and their reactivities are studied. These building blocks are then used for polyfunctionalization, via a modular synthesis approach. Specifically, we are developing a series of fluorinated Julia-Kocienski reagents, where fluorine atom is introduced via metalation-electrophilic fluorination. To gain a deeper understanding of the chemical methodology, reactivities of these reagents are studied in olefination reactions, and also compared with unfluorinated analogs. The overall goal of our work is the development of a “chemical fluoroolefination toolbox” for the synthesis of diverse functionalized fluorinated alkenes. We are also involved with the development of biologically important compounds, such as potential anti-tumor and antiviral agents, via our fluorination chemistry approaches.
In the studies related to the influence of environmental pollutants on human health, we are utilizing fluorine atom to modulate biological activity. In this area, research involves synthesis of fluorinated analogs of environmental pollutants, their putative metabolites and DNA conjugates, for structure activity studies. This often entails the development of stereoselective methodologies, evaluation of chirality in products, and multistep syntheses.
Representative Recent Publications
Mandal, S. K.; Ghosh, A. K.; Kumar, R.; Zajc, B.: Expedient Synthesis of alpha-Substituted Fluoroethenes, Org. Biomol. Chem. 2012, 10, 3164-3167.
Featured on the Front Cover of Issue 16
Kumar, R.; Pradhan, P.; Zajc, B.: Facile Synthesis of 4-Vinyl- and 4-Fluorovinyl-1,2,3-triazoles via Bifunctional “Click-Olefination” Reagents,Chem. Commun. 2011, 3891-3893.
Featured by the Editorial Office on Meet the Authors
Highlighted in Cheminform: DOI: 10.1002/chin.201130128
In Synthesis Special Issue on Fluorine Chemistry
Zajc, B.; Kumar, R.: Synthesis of Fluoroolefins via Julia-Kocienski Olefination, Synthesis 2010, 42, 1822-1836.
Highlighted in Cheminform: DOI: 10.1002/chin.201033244
Ghosh, A. K.; Zajc, B.: Fluorinated 1-Phenyl-1H-tetrazol-5-yl Sulfone Derivatives as General Reagents for Fluoroalkylidene Synthesis, J. Org. Chem. 2009, 74, 8531–8540.
Highlighted in Cheminform: DOI: 10.1002/chin.201013052
Ghosh, A. K.; Banerjee, S.; Sinha, S.; Kang, S. B.; Zajc, B.: alpha-Fluorovinyl Weinreb Amides and alpha-Fluoroenones from a Common Fluorinated Building Block, J. Org. Chem. 2009, 74, 3689-3697.
He, M.; Ghosh, A. K.; Zajc, B.: Julia Olefination as a General Route to Phenyl (alpha-Fluoro)vinyl Sulfones, Synlett 2008, 999-1004.
Highlighted in Cheminform: DOI: 10.1002/chin.200836087
del Solar, M.; Ghosh, A. K.; Zajc, B.: Fluoro-Julia Olefination as a Mild, High-Yielding Route to alpha-Fluoro Acrylonitriles, J. Org. Chem.2008, 73, 8206-8211.
Highlighted in Cheminform: DOI: 10.1002/chin.200911064
Ghosh, A. K.; Lagisetty, P.; Zajc, B.: Direct Synthesis of 8-Fluoro Purine Nucleosides via Metalation-Fluorination, J. Org. Chem. 2007, 72, 8222-8226.
Highlighted in Cheminform: DOI: 10.1002/chin.200810217
Bae, S.; Mah, H.; Chaturvedi, S.; Musafia, T. J.; Baird, W. M.; Katz, A. K.; Carrell, H. L.; Glusker, J. P.; Okazaki, T.; Laali, K. K.; Zajc, B.; Lakshman, M. K.: Synthetic, Crystallographic, Computational and Biological Studies of 1,4-Difluorobenzo[c]phenanthrene and its Metabolites,J. Org. Chem. 2007, 72, 7625-7633.
Zajc, B.; Kake, S: Exceptionally Mild, High-Yield Synthesis of alpha-Fluoro Acrylates, Org. Lett. 2006 8, 4457-4460.
Highlighted in Cheminform: DOI: 10.1002/chin.200702066
Ghosh, A. K.; Zajc, B.: High-Yield Synthesis of Fluorinated Benzothiazolyl Sulfones: General Synthons for Fluoro-Julia Olefinations, Org. Lett.2006, 8, 1553-1556.
Zajc, B. Application of Xenon Difluoride in Synthesis. In Modern Organofluorine Chemistry-Synthetic Aspects. Laali, K., Ed.; Bentham Science Publishers, 2006, Vol. 2, pp 61-157.