chem131links

Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G. J. Chem. Soc. 1966, 1711-1732. The Preparation and Properties of (PPh₃)₃RhCl and some Reactions Thereof including Catalytic Homogeneous Hydrogenation of Olefins and Acetylenes and their Derivatives [no link yet]

Halpern's rules

Hagen, C. M.; Vieille-Petit, L.; Laurenczy, G.; Suess-Fink, G.; Finke, R. G. Organometallics 2005, 24, 1819-1831. Supramolecular Triruthenium Cluster-Based Benzene Hydrogenation Catalysis: Fact or Fiction?

Asymmetric hydrogenation

Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103-151. Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments

Lennon, I. C.; Pilkington, C. J. Synthesis 2003, 11, 1639-1642. The Application of Asymmetric Hydrogenation for the Manufacture of Pharmaceutical Intermediates: The Need for Catalyst Diversity.

Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029-3070. New Chiral Phosphorus Ligands for Enantioselective Hydrogenation.

Blaser, H.-U. Adv. Synth. Catal. 2002, 344, 17-31. The Chiral Switch of (S)-Metolachlor: A Personal Account of an Industrial Odyssey in Asymmetric Catalysis.

Noyori Nobel Lecture 2001

Knowles Nobel Lecture 2001

See Nobel Lectures by Knowles, Noyori and Sharpless on video, plus more stuff on the super Nobel E-Museum site

Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952. Asymmetric Hydrogenation. Rhodium chiral bisphosphine catalyst.

Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754. Asymmetric Hydrogenation of Methyl-(Z)-a-acetamidocinnamate Catalyzed by {1,2-Bis(phenyl-o-anisoyl)phosphino)ethane}rhodium(I): Kinetics, Mechanism, and Origin of Enantioselection

Halpern, J. Science 1982, 217, 401-407. Mechanism and Stereoselectivity of Asymmetric Hydrogenation.

Sun, Y.; Landau, R. N.; Wang, J.; LeBlond, C.; Blackmond, D. G. J. Am. Chem. Soc. 1996, 118, 1348-1353. A Re-Examination of Pressure Effects on Enantioselectivity in Asymmetric Catalytic Hydrogenation. (see homework)

Kitamura, M.; Tsukamoto, M.; Bessho, Y.; Yoshimura, M.; Kobs, U.; Widhalm, M.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6649-6667. Mechanism of Asymmetric Hydrogenation of a-(Acylamino)acrylic Esters Catalyzed by BINAP-Ruthenium(II) Diacetate

Noyori, R.; Ohkuma, T. Angew. Chem. Int. Ed. 2001, 40, 40-73. Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of Ketones.

Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931-7944. Metal-Ligand Bifunctional Catalysis: A Nonclassical Mechanism for Asymmetric Hydrogen Transfer between Alcohols and Carbonyl Compounds

Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144-152. Quantitative Expression of Dynamic Kinetic Resolution of Chirally Labile Enantiomers: Stereoselective Hydrogenation of 2-substituted 3-oxo Carboxylic Esters Catalyzed by BINAP-Ruthenium(II) Complexes

Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370. Substrate-directable Chemical Reactions

hydrosilylation

Stein, J.; Lewis, L. N.; Gao, Y.; Scott, R. A. J. Am. Chem. Soc. 1999, 121, 3693-3703. In Situ Determination of the Active Catalyst in Hydrosilylation Reactions Using Highly Reactive Pt(0) Catalyst Precursors.

is the catalyst homogeneous or heterogeneous?

Widegren, J. A.; Finke, R. G. J. Mol. Catal. A: Chem. 2003, 198, 317-341. A Review of the Problem of Distinguishing True Homogeneous Catalysis from Soluble or Other Metal-particle Heterogeneous Catalysis under Reducing Conditions

Davies, I. W.; Matty, L.; Hughes, D. L.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 10139-10140. Are Heterogeneous Catalysts Precursors to Homogeneous Catalysts?

hydroformylation

Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597-1607. Structural Characterisation in Solution of Intermediates in Rhodium-catalysed Hydroformylation and their Interconversion Pathways.

van der Veen, L. A.; Boele, M. D. K.; Bregman, F. R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J.; Schenk, H.; Bo, C. J. Am. Chem. Soc. 1998, 120, 11616-11626. Electronic Effect on Rhodium Diphosphine Catalyzed Hydroformylation: The Bite Angle Effect Reconsidered

van der Veen, L.; Keeven, P. H.; Schoemaker, G. C.; Reek, J. H. N.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Lutz, M.; Spek, A. L. Organometallics 2000, 19, 872-883. Origin of the Bite Angle Effect on Rhodium Diphosphine Catalyzed Hydroformylation.

Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; Gavney, J. A. J.; Powell, D. R. J. Am. Chem. Soc. 1992, 114, 5535-5543. Diphosphines with Natural Bite angles near 120° Increase Selectivity for n-Aldehyde Formation in Rhodium-Catalyzed Hydroformylation.

Clark, T. P.; Landis, C. R.; Freed, S. L.; Klosin, J.; Abboud, K. A. J. Am. Chem. Soc. 2005, 127, 5040-5042. Highly Active, Regioselective, and Enantioselective Hydroformylation with Rh Catalysts Ligated by Bis-3,4-diazaphospholanes.

hydrocyanation

Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869-9882. Ligand Electronic Effects in Asymmetric Catalysis: Enhanced Enantioselectivity in the Asymmetric Hydrocyanation of Vinylarenes (see homework)

3. CO Chemistry

Sunley, G. J.; Watson, D. J. Catal. Today 2000, 58, 293-307. High Productivity Methanol Carbonylation Catalysis Using Iridium. The Cativa(TM) Process for the Manufacture of Acetic Acid

Ghaffar, T.; Adams, H.; Maitlis, P. M.; Sunley, G. J.; Baker, M. J.; Haynes, A. Chem. Commun. 1998, 1023-1024. Spectroscopic Identification and Reactivity of [Ir(CO)3I2Me], a Key Reactive Intermediate in Iridium Catalyzed Methanol Carbonylation.

Maitlis, P. M. J. Mol. Catal. A: Chem. 2003, 204-205, 54-61. Metal Catalysed CO Hydrogenation: Hetero- or Homo-, What is the Difference?

Maitlis, P. M.; Haynes, A.; Sunley, G. J.; Howard, M. J. J. Chem. Soc., Dalton Trans. 1996, 2187-2196. Methanol Carbonylation Revisited: Thirty Years On [no link yet]

Haynes, A.; Maitlis, P. M.; Morris, G. E.; Sunley, G. J.; Adams, H.; Badger, P. W.; Bowers, C. M.; Cook, D. B.; Elliott, P. I. P.; Ghaffar, T.; Green, H.; Griffin, T. R.; Payne, M.; Pearson, J. M.; Taylor, M. J.; Vickers, P. W.; Watt, R. J. J. Am. Chem. Soc. 2004, 126, 2847-2861. Promotion of Iridium-Catalyzed Methanol Carbonylation: Mechanistic Studies of the Cativa Process.

Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1994, 475, 57-63. Homogeneous Catalysis by Cationic Palladium Complexes. Precision catalysis in the Carbonylation of Alkynes

4. Olefin chemistry

Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. The Development of L₂X₂Ru=CHR Olefin Metathesis Catalysts: An Organometallic Success Story.

La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721. Mo-Catalyzed Asymmetric Synthesis of Dihydrofurans. Catalytic Kinetic Resolution and Enantioselective Desymmetrization through Ring-Closing Metathesis. (see homework)

Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042. Catalytic Enantioselective Ring-Closing Metathesis by a Chiral Biphen-Mo Complex (see homework)

4a. Polyolefins

Ziegler Nobel Lecture 1963

Natta Nobel Lecture 1963

kinetics/mechanism

Landis, C. R.; Rosaaen, K. A.; Sillars, D. R. J. Am. Chem. Soc. 2003, 125, 1710-1711. Direct Observation of Insertion Events at rac-(C2H4(1-indenyl)2)Zr(MeB(C6F5)3)-Polymeryl Intermediates: Distinction between Continuous and Intermittent Propagation Modes

Sillars, D. R.; Landis, C. R. J. Am. Chem. Soc. 2003, 125, 9894-9895. Catalytic Propene Polymerization: Determination of Propagation, Termination, and Epimerization Kinetics by Direct NMR Observation of the (EBI)Zr(MeB(C6F5)3)propenyl Catalyst Species.

Landis, C. R.; Rosaaen, K. A.; Uddin, J. J. Am. Chem. Soc. 2002, 124, 12062-12063. Heavy-Atom Kinetic Isotope Effects, Cocatalysts, and the Propagation Transition State for Polymerization of 1-Hexene Using the rac-(C2H4(1-indenyl)2)ZrMe2 Catalyst Precursor

Liu, Z.; Somsook, E.; White, C. B.; Rosaaen, K. A.; Landis, C. R. J. Am. Chem. Soc. 2001, 123, 11193-11207. Kinetics of Initiation, Propagation, and Termination for the [rac-(C2H4(1-indenyl)2)ZrMe][MeB(C6F5)3]-Catalyzed Polymerization of 1-Hexene.

Grubbs, R. H.; Coates, G. W. Acc. Chem. Res. 1996, 29, 85-93. a-Agostic Interactions and Olefin Insertion in Metallocene Polymerization Catalysts.

oscillating catalysts

Coates, G. W.; Waymouth, R. M. Science 1995, 267, 217-219. Oscillating Stereocontrol: A Strategy for the Synthesis of Thermoplastic Elastomeric Polypropylene

Busico, V.; Castelli, V. V. A.; Aprea, P.; Cipullo, R.; Segre, A.; Talarico, G.; Vacatello, M. J. Am. Chem. Soc. 2003, 125, 5451-5460. "Oscillating" Metallocene Catalysts: What Stops the Oscillation?

alkene-olefin adducts

Carpentier, J.-F.; Wu, Z.; Lee, C. W.; Strömberg, S.; Christopher, J. N.; Jordan, R. F. J. Am. Chem. Soc. 2000, 122, 7750-7767. d0 Metal Olefin Complexes. Synthesis, Structures, and Dynamic Properties of (C5R5)2Zr(OCMe2CH2CH2CH=CH2)+ Complexes: Models for the Elusive (C5R5)2Zr(R)(Olefin)+ Intermediates in Metallocene-Based Olefin Polymerization Catalysis.

Casey, C. P.; Lee, T.-Y.; Tunge, J. A.; Carpenetti, D. W. I. J. Am. Chem. Soc. 2001, 123, 10762-10763. Direct Observation of a Nonchelated Metal-Alkyl-Alkene Complex and Measurement of the Rate of Alkyl Migration to a Coordinated Alkene

Casey, C. P.; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320-4330. Kinetics and Thermodynamics of Alkene Complexation in d0 Metal-Alkyl-Alkene Complexes

catalyst reviews

McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587-2598. Group 4 ansa-Cyclopentadienyl-amido Catalysts for Olefin Polymerization ("constrained-geometry catalysts")

Younkin, T. R.; Connor, E. F.; Henderson, J. I.; Friedrich, S. K.; Grubbs, R. H.; Bansleben, D. A. Science 2000, 287, 460-462. Neutral, Single-Component Nickel (II) Polyolefin Catalysts That Tolerate Heteroatoms.

Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. Engl. 1999, 38, 428-447. The Search for New-Generation Olefin Polymerization Catalysts: Life Beyond Metallocenes.

Drent, E.; Budzelaar, P. H. M. J. Organomet. Chem. 2000, 593-594, 211-225. The Oxo-synthesis Catalyzed by Cationic Palladium Complexes, Selectivity Control by Neutral Ligand and Anion

link here to a 'polymerization of polar monomers' cume exam from 2001

Mecking, S.; Johnson, L. K.; Wang, L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 888-899. Mechanistic Studies of the Palladium-Catalyzed Copolymerization of Ethylene and a-Olefins with Methyl Acrylate

Shultz, C. S.; Ledford, J.; DeSimone, J. M.; Brookhart, M. J. Am. Chem. Soc. 2000, 122, 6351-6356. Kinetic Studies of Migratory Insertion Reactions at the (1,2-Bis(diphenylphosphino)propane)Pd(II) Center and Their Relationship to the Alternating Copolymerization of Ethylene and Carbon Monoxide (see homework)

supported catalysts

Roscoe, S. B.; Frechet, J. M. J.; Walzer, J. F.; Dias, A. J. Science 1998, 280, 270-273. Polyolefin Spheres from Metallocenes Supported on Noninteracting Polystyrene.

several articles in the Chemical Reviews 2000 thematic issue:

Hlatky, G. G. Chem. Rev. 2000, 100, 1347-1376. Heterogeneous Single-Site Catalysts for Olefin Polymerization.

Alt, H. G.; Köppl, A. Chem. Rev. 2000, 100, 1205 -1222. Effect of the Nature of Metallocene Complexes of Group IV Metals on Their Performance in Catalytic Ethylene and Propylene Polymerization

Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169-1203. Late-Metal Catalysts for Ethylene Homo- and Copolymerization.

Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391-1434. Cocatalysts for Metal-Catalyzed Olefin Polymerization: Activators, Activation Processes, and Structure-Activity Relationships.

Coates, G. W. Chem. Rev. 2000, 100, 1223-1252. Precise Control of Polyolefin Stereochemistry Using Single-Site Metal Catalysts

5. Oxidation

Sharpless Nobel Lecture 2001

C+E News 2003 coverage of the original JACS asymmetric epoxidation paper

Andre Charette's lecture notes (U. Montreal) on Sharpless dihydroxylation and related reactions

Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059-1070. Ligand-Accelerated Catalysis. [no link yet]

DelMonte, A. J.; Haller, J.; Houk, K. N.; Sharpless, K. B.; Singleton, D. A.; Strassner, T.; Thomas, A. J. Am. Chem. Soc. 1997, 119, 9907-9908. Experimental and Theoretical Kinetic Isotope Effects for Asymmetric Dihydroxylation. Evidence Supporting a Rate-Limiting "(3 + 2)" Cycloaddition (see homework)

Deubel, D. V.; Frenking, G. Acc. Chem. Res. 2003, 36, 645-651. [3+2] versus [2+2] Addition of Metal Oxides Across C=C Bonds. Reconciliation of Experiment and Theory

Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771. The Osmium-catalyzed Asymmetric Dihydroxylation: a New Ligand Class and a Process Improvement (see homework)

6. Palladium

Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066. The Heck Reaction as a Sharpening Stone of Palladium Catalysis.

Cotter, W. D.; Barbour, L.; McNamara, K. L.; Hechter, R.; Lachicotte, R. J. J. Am. Chem. Soc. 1998, 120, 11016 -11017. Thermodynamics and Mechanism of the Reversible Tin-to-Palladium Transmetalation of the Furyl Group.

Maleczka, R. E., Jr.; Gallagher, W. P.; Terstiege, I. J. Am. Chem. Soc. 2000, 122, 384-385. Stille Couplings Catalytic in Tin: Beyond Proof-of-Principle (see homework)

RajanBabu, T. V. Chem. Rev. 2003, 103, 2845-2860. Asymmetric Hydrovinylation Reaction

Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364. Designing a Receptor for Molecular Recognition in a Catalytic Synthetic Reaction: Allylic Alkylation

de Vries, J. G. Can. J. Chem. 2001, 79, 1086-1092. The Heck Reaction in the Production of Fine Chemicals.

Hayashi, T.; Konishi, M.; Fukushima, M.; Kanehira, K.; Hioki, T.; Kumada, M. J. Org. Chem. 1983, 48, 2195-2202. Chiral (Beta-Aminoalkyl)phosphines. Highly Efficient Phosphine Ligands for Catalytic Asymmetric Grignard Cross-Coupling.

Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028. Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions.

Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688. Catalysts for Cross-Coupling Reactions with Non-activated Alkyl Halides.

Hills, I. D.; Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5749-5752. Toward an Improved Understanding of the Unusual Reactivity of Pd0/Trialkylphosphane Catalysts in Cross-Couplings of Alkyl Electrophiles: Quantifying the Factors That Determine the Rate of Oxidative Addition.

Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 7905-7920. Application of Chiral Mixed Phosphorus/Sulfur Ligands to Palladium-Catalyzed Allylic Substitutions.

Screening

Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123-2132. A Fluorescence-Based Assay for High-Throughput Screening of Coupling Reactions. Application to Heck Chemistry.

Lavastre, O.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1999, 38, 3163-3165. Discovery of Novel Catalysts for Allylic Alkylation with a Visual Colorimetric Assay.

Cooper, A. C.; McAlexander, L. H.; Lee, D.-H.; Torres, M. T.; Crabtree, R. H. J. Am. Chem. Soc. 1998, 120, 9971-9972. Reactive Dyes as a Method for Rapid Screening of Homogeneous Catalysts.

Taylor, S. J.; Morken, J. P. Science 1998, 280, 267-270. Thermographic Selection of Effective Catalysts from an Encoded Polymer-Bound Library.

Reddington, E.; Sapienza, A.; Gurau, B.; Viswanathan, R.; Sarangapani, S.; Smotkin, E. S.; Mallouk, T. E. Science 1998, 280, 1735-1737. Combinatorial Electrochemistry: A Highly Parallel, Optical Screening Method for Discovery of Better Electrocatalysts.

Weinberg, W. H.; Jandeleit, B.; Self, K.; Turner, H. Curr. Opin. Solid State Mater. Sci. 1998, 3, 104-110. Combinatorial Methods in Homogeneous and Heterogeneous Catalysis.

7. Asymmetric catalysis

Blaser, H.-U. Chem. Commun. 2003, 293-296. Enantioselective Catalysis in Fine Chemicals Production

Blaser, H.-U.; Spindler, F.; Studer, M. Appl. Catal. A: General 2001, 221, 119-143. Enantioselective Catalysis in Fine Chemicals Production (same as the 2003 article, but many more details)

privileged reactions and ligands

Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431. Asymmetric Catalysis of Epoxide Ring-Opening Reactions.

Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691-1693. Privileged Chiral Catalysts

making achiral ligands adopt chiral conformations

Katsuki, T. Adv. Synth. Catal. 2002, 344, 131-147. Chiral Metallosalen Complexes: Structures and Catalyst Tuning for Asymmetric Epoxidation and Cyclopropanation (see homework)

Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297-3344. Use of Achiral and Meso Ligands To Convey Asymmetry in Enantioselective Catalysis (see homework)

nonlinear effects

Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923-2959. Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation

Click here for a link to a cume exam on nonlinear effects (2003)

Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362. Mechanistic Investigation Leads to a Synthetic Improvement in the Hydrolytic Kinetic Resolution of Terminal Epoxides.

8. Heterogeneous catalysis

Serafin, J. G.; Liu, A. C.; Seyedmonir, S. R. J. Mol. Catal. A: Chem. 1998, 131, 157-168. Surface Science and the Silver-Catalyzed Epoxidation of Ethylene: an Industrial Perspective

Grasselli, R. K. Catal. Today 1999, 49, 141-153. Advances and Future Trends in Selective Oxidation and Ammoxidation Catalysis.

Maitlis, P. M.; Quyoum, R.; Long, H. C.; Turner, M. L. Appl. Catal. A: General 1999, 186, 363-374. Towards a Chemical Understanding of the Fischer-Tropsch Reaction: Alkene Formation (see homework)

Brady, R. C. I.; Pettit, R. J. Am. Chem. Soc. 1981, 103, 1287-1289. Mechanism of the Fischer-Tropsch Reaction. The Chain Propagation Step

Muetterties, E. L.; Rhodin, T. N.; Band, E.; Brucker, C. F.; Pretzer, W. R. Chem. Rev. 1979, 79, 91-137. Clusters and Surfaces

Sabatier Nobel Lecture 1912

An Introduction to Surface Chemistry Nice web-based lecture notes from Roger Nix, Queen Mary College, University of London. See also the extensive links on their surface science homepage

Syllabus

Links

Comments: Glueck@Dartmouth.Edu

Dartmouth College

Chemistry Department

last revised 9-17-07