David S. Glueck

Professor Glueck received his A.B. and A.M. degrees in chemistry in 1986 from Harvard University, and his PhD. at the University of California, Berkeley, in 1990, with Bob Bergman. After working on crown ethers, intercalation, and buckyballs as an NSF-NATO postdoctoral fellow with Malcolm Green at the Inorganic Chemistry Lab, University of Oxford, he joined the Dartmouth faculty in 1992.

Position: Professor of Chemistry (Chair)
E-Mail: David S. Glueck
Research Group Web Site

Research Interests

I am interested in applications of synthetic chemistry to homogeneous catalysis (especially asymmetric catalysis) and materials science.

We have developed three new catalytic methods for asymmetric synthesis of chiral phosphines, which are a useful class of ligands for metal-catalyzed asymmetric synthesis. In asymmetric hydrophosphination, a chiral Pt(0) complex catalyzes enantioselective addition of a P-H bond across a C=C bond. In asymmetric phosphination, a chiral Pd(0) complex catalyzes enantioselective cross-coupling of an aryl iodide and a secondary phosphine. Our most recent discovery, enantioselective alkylation of secondary phosphines, can be used to prepare chiral bidentate diphosphines. Development of these new reactions is guided by extensive mechanistic studies and characterization of the catalytic intermediates. This work involves synthesis of inorganic, organometallic, and organic (especially organophosphorus) compounds.

Our materials research involves preparation and characterization of metal nanoclusters. We use new surface ligands to control the size and physical properties of these materials, and, in collaboration with Barney Grubbs, prepare metal nanocluster/block copolymer composites. A new materials project involves synthesis of luminescent metal complexes for potential solar energy applications.

Selected Publications 

• Pet, M. A.; Cain, M. F.; Hughes, R. P.; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. J. Organomet. Chem. 2009, 694, 2279-2289. Synthesis and Structure of Ferrocenylmethylphosphines, Their Borane Adducts, and Some Related Derivatives.
• Anderson, B. J.; Guino-o, M. A.; Glueck, D. S.; Golen, J. A.; DiPasquale, A. G.; Liable-Sands, L. M.; Rheingold, A. L. Org. Lett. 2008, 10, 4425–4428. Platinum-Catalyzed Enantioselective Tandem Alkylation/Arylation of Primary Phosphines. Asymmetric Synthesis of P-Stereogenic 1-Phosphaacenaphthenes.
• Anderson, B. J.; Glueck, D. S.; DiPasquale, A. G.; Rheingold, A. L. Organometallics 2008, 27, 4992–5001. Substrate and Catalyst Screening in Platinum-Catalyzed Asymmetric Alkylation of Bis(secondary) Phosphines. Synthesis of an Enantiomerically Pure C₂-Symmetric Diphosphine.
• Glueck, D. S. Dalton Trans. 2008, 5276-5286. Metal-Catalyzed Nucleophilic Carbon–Heteroatom (C–X) Bond Formation: the Role of M–X Intermediates. (invited review)
• Glueck, D. S. Chem. Eur. J. 2008, 14, 7108-7117. Catalytic Asymmetric Synthesis of Chiral Phosphanes. (invited review)
• Glueck, D. S. Coord. Chem. Rev. 2008, 252, 2171-2179. Applications of ³¹P NMR Spectroscopy in Development of M(Duphos)-Catalyzed Asymmetric Synthesis of P-Stereogenic Phosphines (M = Pt or Pd). (invited review)
• Stefanescu, D. M.; Glueck, D. S.; Siegel, R.; Wasylishen, R. E. J. Cluster Sci. 2008, 19, 445-458. Synthesis and Characterization of Gold Nanoparticles with Surface Ligands Derived from a Primary Phosphine.
• Blank, N. F.; Moncarz, J. R.; Brunker, T. J.; Scriban, C.; Anderson, B. J.; Amir, O.; Glueck, D. S.; Zakharov, L. N.; Golen, J. A.; Incarvito, C. D.; Rheingold, A. L. J. Am. Chem. Soc. 2007, 129, 6847-6858. Palladium-Catalyzed Asymmetric Phosphination. Scope, Mechanism, and Origin of Enantioselectivity.
• Scriban, C.; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. Organometallics 2007, 26, 1788-1800. Platinum-Catalyzed Asymmetric Alkylation of a Secondary Phosphine: Mechanism and Origin of Enantioselectivity.
• Brunker, T. J.; Anderson, B. J.; Blank, N. F.; Glueck, D. S.; Rheingold, A. L. Org. Lett. 2007, 9, 1109-1112. Enantioselective Synthesis of P-Stereogenic Benzophospholanes via Palladium-Catalyzed Intramolecular Cyclization.
• Glueck, D. S. Synlett 2007, 2627-2634. Metal-Catalyzed Asymmetric Synthesis of P-Stereogenic Phosphines. (invited review)
• Scriban, C.; Glueck, D. S. J. Am. Chem. Soc. 2006, 128, 2788-2789. Platinum-Catalyzed Asymmetric Alkylation of Secondary Phosphines: Enantioselective Synthesis of P-Stereogenic Phosphines.
• Kovacik, I.; Scriban, C.; Glueck, D. S. Organometallics 2006, 25, 536-539. Regiochemistry of Platinum-Catalyzed Hydrophosphination of a Diene. Formation of the Chiral Diphosphine Et₂PCH(CN)CH(CH₂CH₂CN)PEt₂ via Monophosphine Intermediates.
• Blank, N. F.; McBroom, K. C.; Glueck, D. S.; Kassel, W. S.; Rheingold, A. L. Organometallics 2006, 25, 1742-1748. Chirality Breeding via Asymmetric Phosphination. Palladium-Catalyzed Diastereoselective Synthesis of a P-Stereogenic Phosphine.
• Scriban, C.; Wicht, D. K.; Glueck, D. S.; Zakharov, L. N.; Golen, J. A.; Rheingold, A. L. Organometallics 2006, 25, 3370-3378. Platinum(II) Phosphido Complexes as Metalloligands. Structural and Spectroscopic Consequences of Conversion from Terminal to Bridging Coordination.