Examination of transmetalation pathways and effects in aqueous Suzuki coupling using biomimetic Pd nanocatalysts

Journal of Physical Chemistry C

Volumn 118, Issue 32, 2014, Pages 18543-18553

  Briggs, Beverly D ^a   Pekarek, Ryan T ^a,b   Knecht, Marc R ^a  

^a University of Miami   (United States)

^b University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETICS; CATALYSTS; CHEMICAL BONDS; NANOPARTICLES; SENSITIVITY ANALYSIS;

C-C BOND FORMATION; CHEMICAL SPECIES; COUPLING REACTION; DISUBSTITUTED SUBSTRATES; PD NANO PARTICLE; REACTION CONDITIONS; REACTION EQUILIBRIUM; SUZUKI COUPLINGS;

PALLADIUM;

EID: 84906245032     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp504371q     Document Type: Article

References (47)

1. Thomas, J. M.; Raja, R. Designing Catalysts for Clean Technology, Green Chemistry, and Sustainable Development Annu. Rev. Mater. Res. 2005, 35, 315-350
2. Fihri, A.; Bouhrara, M.; Nekoueishahraki, B.; Basset, J.-M.; Polshettiwar, V. Nanocatalysts for Suzuki Cross-Coupling Reactions Chem. Soc. Rev. 2011, 40, 5181-5203
3. Espinet, P.; Echavarren, A. M. The Mechanisms of the Stille Reaction Angew. Chem., Int. Ed. 2004, 43, 4704-4734
4. Beletskaya, I. P.; Cheprakov, A. V. The Heck Reaction as a Sharpening Stone of Palladium Catalysis Chem. Rev. 2000, 100, 3009-3066
5. Slagt, V. F.; de Vries, A. H. M.; de Vries, J. G.; Kellogg, R. M. Practical Aspects of Carbon-Carbon Coupling Reactions Using Heteroarenes Org. Process. Res. Dev. 2010, 14, 30-47
6. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds Chem. Rev. 1995, 95, 2457-2483
7. Astruc, D. Palladium Nanoparticles as Efficient Green Homogeneous and Heterogeneous Carbon-Carbon Coupling Precatalysts: A Unifying View Inorg. Chem. 2007, 46, 1884-1894
8. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3 rd ed.; John Wiley & Sons, Inc.: New York, NY, 2001.
9. Byers, P. K.; Canty, A. J.; Crespo, M.; Puddephatt, R. J.; Scott, J. D. Reactivity and Mechanism in Oxidative Addition to Palladium(II) and Reductive Elimination From Palladium(IV) and an Estimate of the Palladium Methyl Bond Energy Organometallics 1988, 7, 1363-1367
10. Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. Boronic Acids: New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization of an Oxidative-Addition Adduct Generated under Remarkably Mild Conditions J. Am. Chem. Soc. 2002, 124, 13662-13663
11. Amatore, C.; Jutand, A.; Le Duc, G. Kinectic Data for the Transmetalation/Reductive Elimination in Palladium-Catalyzed Suzuki-Miyaura Reactions: Unexpected Triple Role of Hydroxide Ions Used as Base Chem. - Eur. J. 2011, 17, 2492-2503
12. Amatore, C.; Le Duc, G.; Jutand, A. Mechanism of Palladium-Catalyzed Suzuki-Miyaura Reactions: Multiple and Antagonistic Roles of Anionic "Bases" and Their Countercations Chem. - Eur. J. 2013, 19, 10082-10093
13. Carrow, B. P.; Hartwig, J. F. Distinguishing Between Pathways for Transmetalation in Suzuki-Miyaura Reactions J. Am. Chem. Soc. 2011, 133, 2116-2119
14. Pacardo, D. B.; Sethi, M.; Jones, S. E.; Naik, R. R.; Knecht, M. R. Biomimetic Synthesis of Pd Nanocatalysts for the Stille Coupling Reaction ACS Nano 2009, 3, 1288-1296
15. Stille, J. K. The Palladium-Catalyzed Cross-Coupling Reactions of Organotin Reagents with Organic Electrophiles Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524
16. Martin, R.; Buchwald, S. L. Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands Acc. Chem. Res. 2008, 41, 1461-1473
17. Miura, M. Rational Ligand Design in Constructing Efficient Catalyst Systems for Suzuki-Miyaura Coupling Angew. Chem., Int. Ed. 2004, 43, 2201-2203
18. Diallo, A. K.; Ornelas, C.; Salmon, L.; Aranzaes, J. R.; Astruc, D. "Homeopathic" Catalytic Activity and Atom-Leaching Mechanism in Miyaura-Suzuki Reactions under Ambient Conditions with Precise Dendrimer-Stabilized Pd Nanoparticles Angew. Chem., Int. Ed. 2007, 46, 8644-8648
19. Ornelas, C.; Diallo, A. K.; Ruiz, J.; Astruc, D. "Click" Polymer-Supported Palladium Nanoparticles as Highly Efficient Catalysts for Olefin Hydrogenation and Suzuki Coupling Reactions under Ambient Conditions Adv. Synth. Catal. 2009, 351, 2147-2154
20. Narayanan, R.; El-Sayed, M. A. Effect of Colloidal Catalysis on the Nanoparticle Size Distribution: Dendrimer-Pd vs PVP-Pd Nanoparticles Catalyzing the Suzuki Coupling Reaction J. Phys. Chem. B 2004, 108, 8572-8580
21. Pérez-Lorenzo, M. Palladium Nanoparticles as Efficient Catalysts for Suzuki Cross-Coupling Reactions J. Phys. Chem. Lett. 2012, 3, 167-174
22. Gaikwad, A. V.; Holuigue, A.; Thathagar, M. B.; ten Elshof, J. E.; Rothenberg, G. Ion- and Atom-Leaching Mechanisms from Palladium Nanoparticles in Cross-Coupling Reactions Chem. - Eur. J. 2007, 13, 6908-6913
23. Xu, J.; Wilson, A. R.; Rathmell, A. R.; Howe, J.; Chi, M.; Wiley, B. J. Synthesis and Catalytic Properties of Au-Pd Nanoflowers ACS Nano 2011, 5, 6119-6127
24. Pacardo, D. B.; Slocik, J. M.; Kirk, K. C.; Naik, R. R.; Knecht, M. R. Interrogating the Catalytic Mechanism of Nanoparticle Mediated Stille Coupling Reactions Employing Bio-Inspired Pd Nanocatalysts Nanoscale 2011, 3, 2194-2201
25. Miyaura, N. Cross-Coupling Reaction of Organoboron Compounds Via Base-Assisted Transmetalation to Palladium(II) Complexes J. Organomet. Chem. 2002, 653, 54-57
26. Braga, A. A. C.; Morgon, N. H.; Ujaque, G.; Maseras, F. Computational Characterization of the Role of the Base in the Suzuki-Miyaura Cross-Coupling Reaction J. Am. Chem. Soc. 2005, 127, 9298-9307
27. Smith, G. B.; Dezeny, G. C.; Hughes, D. L.; King, A. O.; Verhoeven, T. R. Mechanistic Studies of the Suzuki Cross-Coupling Reaction J. Org. Chem. 1994, 59, 8151-8156
28. Coppage, R.; Slocik, J. M.; Sethi, M.; Pacardo, D. B.; Naik, R. R.; Knecht, M. R. Elucidation of Peptide Effects that Control the Activity of Nanoparticles Angew. Chem., Int. Ed. 2010, 49, 3767-3770
29. Diamanti, S.; Elsen, A.; Naik, R.; Vaia, R. Relative Functionality of Buffer and Peptide in Gold Nanoparticle Formation J. Phys. Chem. C 2009, 113, 9993-9997
30. Nam, K. T.; Lee, Y. J.; Krauland, E. M.; Kottmann, S. T.; Belcher, A. M. Peptide-Mediated Reduction of Silver Ions on Engineered Biological Scaffolds ACS Nano 2008, 2, 1480-1486
31. Lee, Y. J.; Yi, H.; Kim, W.-J.; Kang, K.; Yun, D. S.; Strano, M. S.; Ceder, G.; Belcher, A. M. Fabricating Genetically Engineered High-Power Lithium-Ion Batteries Using Multiple Virus Genes Science 2009, 324, 1051-1055
32. Coppage, R.; Slocik, J. M.; Briggs, B. D.; Frenkel, A. I.; Heinz, H.; Naik, R. R.; Knecht, M. R. Crystallographic Recognition Controls Peptide Binding for Bio-Based Nanomaterials J. Am. Chem. Soc. 2011, 133, 12346-12349
33. Pandey, R. B.; Heinz, H.; Feng, J.; Farmer, B. L.; Slocik, J. M.; Drummy, L. F.; Naik, R. R. Adsorption of Peptides (A3, Flg, Pd2, Pd4) on Gold and Palladium Surfaces by a Coarse-Grained Monte Carlo Simulation Phys. Chem. Chem. Phys. 2009, 11, 1989-2001
34. Coppage, R.; Slocik, J. M.; Briggs, B. D.; Frenkel, A. I.; Naik, R. R.; Knecht, M. R. Determining Peptide Sequence Effects that Control the Size, Structure, and Function of Nanoparticles ACS Nano 2012, 6, 1625-1636
35. Coppage, R.; Slocik, J. M.; Ramezani-Dakhel, H.; Bedford, N. M.; Heinz, H.; Naik, R. R.; Knecht, M. R. Exploiting Localized Surface Binding Effects to Enhance the Catalytic Reactivity of Peptide-Capped Nanoparticles J. Am. Chem. Soc. 2013, 135, 11048-11054
36. Chan, W. C.; White, P. D. Fmoc Solid Phase Peptide Synthesis: A Practical Approach; Oxford University Press: New York, NY, 2000.
37. Shell Particles J. Phys. Chem. B 2000, 104, 6683-6685
38. Creighton, J. A.; Eadon, D. G. Ultraviolet-Visible Absorption Spectra of the Colloidal Metallic Elements J. Chem. Soc., Faraday Trans. 1991, 87, 3881-3891
39. Khalily, M. A.; Ustahuseyin, O.; Garifullin, R.; Genc, R.; Guler, M. O. A Supramolecular Peptide Nanofiber Templated Pd Nanocatalyst for Efficient Suzuki Coupling Reactions Under Aqueous Conditions Chem. Commun. 2012, 48, 11358-11360
40. Sawoo, S.; Srimani, D.; Dutta, P.; Lahiri, R.; Sarkar, A. Size Controlled Synthesis of Pd Nanoparticles in Water and Their Catalytic Application in C-C Coupling Reactions Tetrahedron 2009, 65, 4367-4374
41. Mondal, M.; Bora, U. An Efficient Protocol for Palladium-Catalyzed Ligand-Free Suzuki-Miyaura Coupling in Water Green Chem. 2012, 14, 1873-1876
42. Fihri, A.; Luart, D.; Len, C.; Solhy, C.; Chevrin, C.; Polshettiwar, V. Suzuki-Miyaura Cross-Coupling Coupling Reactions with Low Catalyst Loading: A Green and Sustainable Protocol in Pure Water Dalton Trans. 2011, 40, 3116-3121
43. Dewar, M. J. S.; Jones, R. New Heteroaromatic Compounds. XXV. Studies of Salt Formation in Boron Oxyacids by Boron-11 Nuclear Magnetic Resonance J. Am. Chem. Soc. 1967, 89, 2408-2410
44. Butters, M.; Harvey, J. N.; Jover, J.; Lennox, A. J. J.; Lloyd-Jones, G. C.; Murray, P. M. Aryl Trifluoroborates in Suzuki-Miyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride Angew. Chem., Int. Ed. 2010, 49, 5156-5160
45. Brady, J. E.; Russell, J. W.; Holum, J. R. Chemistry Matter and Its Changes, 3 rd ed.; John Wiley & Sons, Inc.: New York, NY, 2000.
46. Darwent, B. d. Bond Dissociation Energies in Simple Molecules; U.S. Department of Commerce, National Bureau of Standards: Washington, DC, 1970.
47. Pacardo, D. B.; Knecht, M. R. Exploring the Mechanism of Stille C-C Coupling via Peptide-Capped Pd Nanoparticles Results in Low Temperature Reagent Selectivity Catal. Sci. Technol. 2013, 3, 745-753