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David B. Collum
Betty R. Miller Professor
Baker Laboratory, Room 482
dbc6@cornell.edu
607-255-4879
Educational Background
- PhD, Columbia University
- MS, Columbia University
- MA, Columbia University
- BS, Cornell University
Website(s)
Overview
The Collum group studies how aggregation and solvation dictate the reactivity and selectivity of organolithium compounds commonly used by synthetic chemists in both academia and the pharmaceutical industry. A combination of spectroscopic, kinetic, and computational methods bridge organic, organometallic, and analytical chemistry.
Keywords
Physical organic chemistry, organolithium chemistry, kinetics and reaction mechanism
Departments/Programs
- Chemistry and Chemical Biology
Graduate Fields
- Chemistry and Chemical Biology
Research
The importance of organolithium reagents in organic chemistry is indisputable. Reports of the effects of solvents, reaction temperatures, additives, internal coordinating functionalities, electrophile structures, and substituents on product distributions pervade the literature. Nevertheless, complexities resulting from aggregation and solvation render our understanding of the origins of the reactivities and selectivities limited at best. Our group investigates the structural and mechanistic basis of selectivity using a range of spectroscopic, kinetic, and computational methods. A number of projects are in collaboration with pharmaceutical process groups.
Courses
Publications
- Solution Structures of Lithium Amino Alkoxides Used in Highly Enantioselective 1,2-Additions. Bruneau, A. M.; Collum, D. B. J. Am. Chem. Soc. 2014, 53, 2885.
- Method of Continuous Variations: Applications of Job Plots to the Study of Molecular Associations in Organometallic Chemistry. Renny, J. S.; Tomasevich, L. L.; Tallmadge, E. H.; Collum, D. B. Angew. Chem., Int. Ed. 2013, 52, 11998.
- Enediolate-Dilithium Amide Mixed Aggregates in the Enantioselective Alkylation of Arylacetic Acids: Structural Studies and a Stereochemical Model. Ma, Y.; Stivala, C. E.; Wright, A. M.; Hayton, T.; Liang, J.; Keresztes, I.; Lobkovsky, E.; Collum, D. B.; Zakarian, Z. J. Am. Chem. Soc. 2013, 135, 16853.
- Azaaldol Condensation of a Lithium Enolate Solvated by N,N,N’,N’ Tetramethylethylenediamine: Dimer-Based 1,2-Addition to Imines. De Vries, T. S.; Bruneau, A. M.; Liou, L. R.; Subramanian, H.; Collum, D. B. J. Am. Chem. Soc. 2013, 135, 4214.
- Regioselective Lithium Diisopropylamide-Mediated Ortholithiation of 1-Chloro-3-(trifluoromethyl)benzene: Role of Autocatalysis, Lithium Chloride Catalysis, and Reversibility. Hoepker, A. C.; Gupta, L.; Ma, Y.; Faggin, M. F.; Collum, D. B. J. Am. Chem. Soc. 2011, 133, 7135.