David S. Glueck

Academic Appointments

Professor of Chemistry

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

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We have developed several catalytic methods for asymmetric synthesis of chiral phosphines, which are a useful class of ligands for metal-catalyzed asymmetric synthesis, including (a) asymmetric hydrophosphination, in which a chiral Pt(0) complex catalyzes enantioselective addition of a P-H bond across a C=C bond (b) asymmetric phosphination, where a chiral Pd(0) complex catalyzes enantioselective cross-coupling of an aryl iodide and a secondary phosphine, and (c) Pt- or Cu-catalyzed enantioselective alkylation of secondary phosphines, which can be used to prepare chiral bidentate diphosphines. More recently, we have discovered new routes to highly enantiomerically enriched P-stereogenic phosphiranes and secondary phosphine oxides (SPOs).  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.

In another application of asymmetric catalysis, we are studying metal-catalyzed hydration of nitriles, a useful process in the pharmaceutical industry.  This project uses our new chiral SPOs in chiral metal complexes designed to selectively bind and hydrate chiral nitriles.

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646-1568
305 Burke
HB 6128
Department(s): 
Chemistry
Education: 
A.B. Harvard University, 1986
A.M. Harvard University, 1986
Ph.D. University of California at Berkeley, 1990

Selected Publications

Glueck, D. S. Catalytic Asymmetric Synthesis of P-Stereogenic Phosphines: Beyond Precious Metals. Synlett, in press, 2021.

Zimmerman, A. N.; Xu, R. S.; Reynolds, S. C.; Shipp, C. A.; Marshall, D. J.; Wang, G.; Blank, N. F.; Gibbons, S. K.; Hughes, R. P.; Glueck, D. S.; Balaich, G. J.; Rheingold, A. L. Diastereoselective Synthesis of P-Stereogenic Secondary Phosphine Oxides (SPOs) Bearing a Chiral Substituent by Ring Opening of (+)-Limonene Oxide with Primary Phosphido Nucleophiles. J. Org. Chem. 2020, 85, 14516–14526.

Scheetz, P. M.; Chachula, S. T.; Hughes, R. P.; Glueck, D. S.; Moore, C. E.; Gembicky, M.; Rheingold, A. L. Synthesis, Structure, Dynamics, and Enantioface-Selective η3-Benzyl Coordination in the Chiral Rhodium Complexes Rh(diphos*)(η3-CH2Ph). Organometallics 2020, 39, 3802–3816.

Glueck, D. S. Metal–Catalyzed P–C Bond Formation via P–H Oxidative Addition: Fundamentals and Recent Advances. J. Org. Chem. 2020, 85, 14276–14285.

Gibbons, S. K.; Valleau, C. R. D.; Peltier, J. L.; Cain, M. F.; Hughes, R. P.; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. Diastereoselective Coordination of P-Stereogenic Secondary Phosphines in Copper(I) Chiral Bis(phosphine) Complexes: Structure, Dynamics, and Generation of Phosphido Complexes. Inorg. Chem. 2019, 58, 8854-8865.

Glueck, D. S. Modern Aspects of 31P NMR Spectroscopy. In Organophosphorus Chemistry: from Molecules to Applications; Iaroshenko, V., Ed.; Wiley-VCH: Weinheim, 2019, p 457-498.

 Gibbons, S. K.; Xu, Z.; Hughes, R. P.; Glueck, D. S.; Rheingold, A. L. Chiral Bis(Phospholane) PCP Pincer Complexes: Synthesis, Structure, and Nickel-Catalyzed Asymmetric Phosphine Alkylation. Organometallics 2018, 37, 2159–2166.

Scheetz, P. M.; Blank, N. F.; Gibbons, S. K.; Glueck, D. S.; Rheingold, A. L. Oxidative Addition of Methylene Chloride to Me-DuPhos Complexes of Palladium and Rhodium. Inorg. Chim. Acta 2018, 483, 111-115.

Wang, G.; Gibbons, S. K.; Glueck, D. S.; Sibbald, C.; Fleming, J. T.; Higham, L. J.; Rheingold, A. L. Copper–Phosphido Intermediates in Cu(IPr)-Catalyzed Synthesis of 1-Phosphapyracenes via Tandem Alkylation/Arylation of Primary Phosphines. Organometallics 2018, 37, 1760–1772.

Deegan, M. M.; Muldoon, J. A.; Hughes, R. P.; Glueck, D. S.; Rheingold, A. L. Synthesis and Structure of Metal Complexes of P-Stereogenic Chiral Phosphiranes: An EDA-NOCV Analysis of the Donor–Acceptor Properties of Phosphirane Ligands. Organometallics 2018, 37, 1473–1482.

Muldoon, J. A.; Varga, B. R.; Deegan, M. M.; Chapp, T. W.; Eördögh, Á. M.; Hughes, R. P.; Glueck, D. S.; Moore, C. E.; Rheingold, A. L. Inversion of Configuration at the Phosphorus Nucleophile in Diastereoselective and Enantioselective Synthesis of P-Stereogenic syn-Phosphiranes from Chiral Epoxides. Angew. Chem. Int. Ed. 2018, 57, 5047–5051.

Glueck, D. S. 1,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene (S,S)-Me-DuPhos and 1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene (R,R)-Me-DuPhos, First Update.  In e-EROS Encyclopedia of Reagents for Organic Synthesis; John Wiley and Sons: 2018.

 

Scheetz, P. M.; Glueck, D. S.; Rheingold, A. L. Rhodium-Catalyzed Isomerization of a Bis(secondary phosphine) to an Unsymmetrical Diphosphine via P–C Cleavage and P–P and C–H Bond Formation. Organometallics 2017, 36, 3387–3397.

Gibbons, S. K.; Hughes, R. P.; Glueck, D. S.; Royappa, A. T.; Rheingold, A. L.; Arthur, R. B.; Nicholas, A. D.; Patterson, H. H. Synthesis, Structure, and Luminescence of Copper(I) Halide Complexes of Chiral Bis(phosphines). Inorg. Chem. 2017, 56, 12809–12820.

Anderson, B. J.; Reynolds, S. C.; Guino-o, M. A.; Xu, Z.; Glueck, D. S. Effect of Linker Length on Selectivity and Cooperative Reactivity in Platinum-Catalyzed Asymmetric Alkylation of Bis(phenylphosphino)alkanes. ACS Catal. 2016, 6, 8106–8114.

Wang, G.; Guino-o, M. A.; Glueck, D. S.; Golen, J. A.; Daley, C. J. A.; Rheingold, A. L. Synthesis of a Phosphapyracene via Metal-Mediated Cyclization: Structural and Reactivity Effects of Acenaphthene Precursors. Dalton Trans. 2015, 44, 9943–9954.

Emerson, E. W.; Cain, M. F.; Sanderson, M. D.; Knarr, C. B.; Glueck, D. S.; Ahern, J. C.; Patterson, H. H.; Rheingold, A. L. Synthesis, structure, and luminescence of the “octahedral” cluster Cu4I4(rac-IsMePCH2PMeIs)2 (Is = 2,4,6-(i-Pr)3C6H2). Inorg. Chim. Acta 2015, 427, 168-172.

Xu, Z.; Cain, M. F.; Rupert, A. V.; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. Selective formation of a C3-symmetric P-stereogenic tris(phosphine) via platinum-catalyzed asymmetric alkylation of a tris(secondary phosphine). Tetrahedron: Asymmetry 2015, 26, 1459–1468.

Reynolds, S. C.; Hughes, R. P.; Glueck, D. S.; Rheingold, A. L. Org. Lett. 2012, 14, 4238–4241. Synthesis, Reactivity, and Resolution of a C2–Symmetric, P–Stereogenic Benzodiphosphetane, a Building Block for Chiral Bis(phosphines).

Guino-o, M. A.; Zureick, A. H.; Blank, N. F.; Anderson, B. J.; Chapp, T. W.; Kim, Y.; Glueck, D. S.; Rheingold, A. L. Organometallics 2012, 31, 6900-6910. Synthesis and Structure of Platinum Bis(phospholane) Complexes Pt(diphos*)(R)(X), Catalyst Precursors for Asymmetric Phosphine Alkylation.

Chapp, T. W.; Schoenfeld, A. J.; Sanderson, M. D.; Chang, C. L.; Glueck, D. S.; Golen, J. A.; Moore, C. E.; Rheingold, A. L. Organometallics 2012, 31, 5573–5585. Synthesis, Structure, Dynamics, and Selective Methylation of Platinum and Palladium Diphosphametallacyclobutane Complexes.

Cain, M. F.; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. Organometallics 2012, 31, 775-778. Asymmetric Synthesis and Metal Complexes of a C3-Symmetric P-Stereogenic Triphosphine, (R)-MeSi(CH2PMe(t-Bu))3 (MT-Siliphos).

Zuzek, A. A.; Reynolds, S. C.; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. Organometallics 2011, 30, 1812-1817. Synthesis and Structure of Gold and Platinum Menthyl Complexes.

Seibert, A. R.; Cain, M. F.; Glueck, D. S.; Nataro, C. J. Organomet. Chem.2011, 696, 2259-2262. Electrochemistry of P(CH2Fc)3 and derivatives.

Glueck, D. S. Catal. Sci. Technol. 2011, 1, 1099-1108. Selectivity via catalyst or substrate control in catalytic asymmetric transformations of bifunctional symmetrical substrates. (invited review)

Cain, M. F.; Reynolds, S. C.; Anderson, B. J.; Glueck, D. S.; Golen, J. A.; Moore, C. E.; Rheingold, A. L. Inorg. Chim. Acta 2011, 369, 55-61. Synthesis, Structure and Spectroscopic Properties of 2,3-bis(diphenylphosphino)quinoxaline (dppQx) and Its Copper(I) Complexes. (special R.G. Bergman issue)

Cain, M. F.; Hughes, R. P.; Glueck, D. S.; Golen, J. A.; Moore, C. E.; Rheingold, A. L. Inorg. Chem.2010, 49, 7650–7662. Synthesis and Structure of Intermediates in Copper-Catalyzed Alkylation of Diphenylphosphine. (cover picture)

Glueck, D. S. Top. Organomet. Chem.2010, 31, 65-100. Recent Advances in Metal-Catalyzed C–P Bond Formation. (invited review)

Lane, E. M.; Chapp, T. W.; Hughes, R. P.; Glueck, D. S.; Feland, B. C.; Bernard, G. M.; Wasylishen, R. E.; Rheingold, A. L. Inorg. Chem.2010, 49, 3950–3957. Synthesis of Gold Phosphido Complexes Derived from Bis(secondary) Phosphines. Structure of Tetrameric [Au(MesP(CH2)3PMes)Au]4.

Chapp, T. W.; Schoenfeld, A. J.; Glueck, D. S. Organometallics2010, 29, 2465-2473. Effects of Linker Length on the Rate and Selectivity of Platinum-Catalyzed Asymmetric Alkylation of the Bis(isitylphosphino)alkanes IsHP(CH2)nPHIs (Is = 2,4,6-(i-Pr)3C6H2, n = 1–5).

Chapp, T. W.; Glueck, D. S.; Golen, J. A.; Moore, C. E.; Rheingold, A. L. Organometallics2010, 29, 378-388. Platinum-Catalyzed Asymmetric Alkylation of Bis(isitylphosphino)ethane: Stereoselectivity Reversal in Successive Formation of Two P-C Bonds.

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Works in progress

“Metal-catalyzed Asymmetric Synthesis of P-Stereogenic Phosphines”