Dr. Patrick H. Toy　　　蔡顯輝博士

B.Sc. Ohio State University;
Ph.D. Wayne State University

Room 404
Chong Yuet Ming Chemistry Building
The University of Hong Kong
Pokfulam Road
Hong Kong

1. June 1998 – June 2000: Post-Doctoral Research Associate, The Scripps Research Institute, La Jolla, California
2. July 2000 – September 2001: Research Scientist, Wyeth, Pearl River, New York
3. October 2001 – May 2007: Assistant Professor, The University of Hong Kong, Hong Kong
4. June 2007 – present: Associate Professor, The University of Hong Kong, Hong Kong
   

We are interested in developing new variations of the Morita-Baylis-Hillman reaction and improved catalysts for performing them.

Furthermore, we have developed the first example of a catalytic Mitsunobu reaction and are working to further optimize the process.

 

Development of Solid-Phase Organic Synthesis Supports

Polymer-Supported Catalysts, Reagents and Ligands

University of Hong Kong Publications:

1. Cividino, P.; Dheu-Andries, M.-L.; Ou, J.; Milet, A.; Py, S.; Toy, P. H. Mechanistic Investigations of the Tributylphospine-Mediated Nitrone Reduction Reaction and Its Application in Cyclic Imine Synthesis. Tetrahedron Lett. In press.

2. Lu, J.; Toy, P. H. Organic Polymer Supports for Synthesis and for Reagent and Catalyst Immobilization. Chem. Rev. 2009, 109, 815-838. [PDF]

3. Lam, Y.-L.; Yang, D.; Chan, C.-Y.; Chan, K.-Y.; Toy, P. H. Use of Water-Compatible Polystyrene-Polyglycidol Resin for the Separation and Recovery of Dissolved Precious Metal Salts. Ind. Chem. Eng. Res. 2009, 48, 4975-4979. [PDF]

4. Kwong, C. K.-W.; Fu, M. Y.; Lam, C. S.-L.; Toy, P. H. The Phosphine-Catalyzed Alkyne to 1,3-Diene Isomerization Reaction. Synthesis 2008, 2307-2317. [PDF]

5. He, R.; Toy, P. H.; Lam, Y. Polymer-Supported Hantzsch 1,4-Dihydropyridine Ester: An Efficient Biomimetic Hydrogen Source. Adv. Synth. Catal. 2008, 350, 54-60. [PDF]

6. But, T. Y. S.; Toy, P. H. The Mitsunobu Reaction: Origin, Mechanism, Improvements and Applications. Chem. Asian J. 2007, 2, 1340-1355. [PDF]

7. Yamamoto, Y.; Kawano, Y.; Toy, P. H.; Togo, H. PhI- and Polymer-Supported PhI-Catalyzed Oxidative Conversion of Ketones and Alcohols to a-Tosyloxyketones with m-Chloroperbenzoic Acid and p-Toluenesulfonic Acid. Tetrahedron 2007, 63, 4680-4687. [PDF]

8. Shang, Y.; But, T. Y. S.; Togo, H.; Toy, P. H. Macroporous Polystyrene-Supported (Diacetoxyiodo)benzene: An Efficient Heterogeneous Oxidizing Reagent. Synlett 2007, 67-70. [PDF]

9. Kwong, C. K.-W.; Huang, R.; Zhang, M.; Shi, M.; Toy, P. H. Bifunctional Polymeric Organocatalysts and Their Application in the Cooperative Catalysis of Morita-Baylis-Hillman Reactions. Chem. Eur. J. 2007, 13, 2369-2376. [PDF]

10. Chung, C. W. Y.; Toy, P. H. Multipolymer Reaction System for Selective Aerobic Alcohol Oxidation: Use of Multiple Different Polymer-Supported Ligands. J. Comb. Chem. 2007, 9, 115-120. [PDF] [Supporting Info]

11. Toy, P. H. Nanoscale Catalysis of Organic Molecule Transformations. J. Exp. Nanosci. 2006, 1, 397. [PDF]

12. But, T. Y. S.; Toy, P. H. Organocatalytic Mitsunobu Reactions. J. Am. Chem. Soc. 2006, 128, 9636-9637. [PDF] [Supporting Info]

Highlighted at: http://www.organic-chemistry.org/abstracts/lit1/373.shtm

13. He, H. S.; Yan, J. J.; Shen, R.; Zhuo, S.; Toy, P. H. Non-Cross-Linked Polystyrene-Supported Triphenylphosphine Microencapsulated Palladium: An Efficient and Recyclable Catalyst for Suzuki-Miyaura Reactions. Synlett 2006, 563-566. [PDF]

14. Teng, W.-D.; Huang, R.; Kwong, C. K.-W.; Shi, M.; Toy, P. H. Influence of Michael Acceptor Stereochemistry on Intramolecular Morita-Baylis-Hillman Reactions. J. Org. Chem. 2006, 71, 368-371. [PDF] [Supporting Info]

15. Kan, J. T. Z.; Toy, P. H. Sulfur- and Selenium-Based Linkers in Polymer-Supported Organic Synthesis. J. Sulfur Chem. 2005, 26, 509-540. [PDF]

16. He, H. S.; Zhang, C.; Ng, C. K.-W.; Toy, P. H. Polystyrene-Supported Triphenylarsines: Useful Ligands in Palladium-Catalyzed Aryl Halide Homocoupling Reactions and a Catalyst for Alkene Epoxidation Using Hydrogen Peroxide. Tetrahedron 2005, 61, 12053-12057. [PDF]

17. Zhao, L.-J.; Kwong, C. K.-W.; Shi, M.; Toy, P. H. Optimization of Polystyrene-Supported Triphenylphosphine Catalysts for Aza-Morita-Baylis-Hillman Reactions. Tetrahedron 2005, 61, 12026-12032. [PDF]

18. Toy, P. H.; Shi, M. Polymer-Supported Reagents and Catalysts: Increasingly Important Tools for Organic Synthesis. Tetrahedron 2005, 61, 12025. [PDF]

19. But, T. Y. S.; Tashino, Y.; Togo, H.; Toy, P. H. A Multipolymer System for Organocatalytic Alcohol Oxidation. Org. Biomol. Chem. 2005, 3, 970-971. [PDF]

20. He, H. S.; Chung, C. W. Y.; But, T. Y. S.; Toy, P. H. Arsonium Ylides in Organic Synthesis. Tetrahedron 2005, 61, 1385-1405. [PDF]

21. Chung, C. W. Y.; Toy, P. H. A Polystyrene-Supported Triflating Reagent for the Synthesis of Aryl Triflates. Tetrahedron 2005, 61, 709-715. [PDF]

22. Harned, A. M.; He, H. S.; Toy, P. H.; Flynn, D. L.; Hanson, P. R. Multipolymer Solution-Phase Reactions: Application to the Mitsunobu Reaction. J. Am. Chem. Soc. 2005, 127, 52-53. [PDF] [Supporting Info 1 2 3]

23. Lau, K. C. Y.; He, H. S.; Chiu, P.; Toy, P. H. Polystyrene-Supported Triphenylarsine Reagents and Their Use in Suzuki Cross-Coupling Reactions. J. Comb. Chem. 2004, 6, 955-960. [PDF] [Supporting Info]

24. Zhao, L.-J.; He, H. S.; Shi, M.; Toy, P. H. Polystyrene-Supported Phosphine Catalyzed Aza-Baylis-Hillman Reactions and the Relationship Between Resin Loading Level and Catalyst Efficiency. J. Comb. Chem. 2004, 6, 680-683. [PDF] [Supporting Info 1 2]

25. Kan, J. T. W.; Toy, P. H. Poly(Ethylene Glycol)-Supported a,a,a-Trifluoroacetophenone in Dioxirane Mediated Alkene Epoxidation Reactions. Tetrahedron Lett. 2004, 45, 6357-6359. [PDF]

26. Choi, M. K. W.; Toy, P. H. An Improved and General Synthesis of Monomers for Incorporating Trityl Linker Groups into Polystyrene Synthesis Supports. Tetrahedron 2004, 60, 2903-2907. [PDF]

27. Choi, M. K. W.; Toy, P. H. Polymer-Supported Thioanisole: A Versatile Platform for Organic Synthesis Reagents. Tetrahedron 2004, 60, 2875-2879. [PDF]

28. Chung, C. W. Y.; Toy, P. H. Chiral Auxiliaries in Polymer-Supported Organic Synthesis. Tetrahedron: Asymmetry 2004, 15, 387-399. [PDF]

29. Choi, M. K. W.; He, H. S.; Toy, P. H. Direct Radical Polymerization of 4-Styryldiphenylphosphine: Preparation of Cross-Linked and Non-Cross-Linked Triphenylphosphine Containing Polystyrene Polymers. J. Org. Chem. 2003, 68, 9831-9834. [PDF] [Supporting Info]

30. Choi, M. K. W.; Toy, P. H. Soluble Polystyrene-Based Sulfoxide Reagents for Swern Oxidation Reactions. Tetrahedron 2003, 59, 7171-7176. [PDF]

University of Hong Kong Publications (with Prof. David L. Phillips):

31. Ma, C.; Kwok, W. M.; Chan, W. S.; Du, Y.; Zuo, P.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. Time-Resolved Spectroscopy Studies of the Photodeprotection Reactions of p-Hydroxyphenacyl Ester Phototrigger Compounds. Curr. Sci. 2009, 97, 202-209.

32. Xue, J.; Chan, P. Y.; Du, Y.; Guo, Z.; Chung, C. W. Y.; Toy, P. H.; Phillips, D. L. Time-Resolved Resonance Raman Investigation of the 2-Fluorenylnitrenium Ion Reactions with C8 Guanosine Derivatives. J. Phys. Chem. B 2007, 111, 12676-12684. [PDF] [Supporting Info]

33. Ma, C.; Kwok, W. M.; Chan, W. S.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. Ultrafast Time-Resolved Transient Absorption and Resonance Raman Spectroscopy Study of the Photodeprotection and Rearrangement Reaction of p-Hydroxylphenacyl Caged Diethyl Phosphate. J. Am. Chem. Soc. 2006, 128, 2558-2570. [PDF] [Supporting Info]

34. Ma, C.; Kwok, W. M.; Chan, W. S.; Zuo, P.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. Ultrafast Time-Resolved Study of Photophysical Processes Involved in the Photodeprotection of p-Hydroxyphenacyl Caged Phototrigger Compounds. J. Am. Chem. Soc. 2005, 127, 1463-1472. [PDF] [Supporting Info]

35. Ma, C.; Zuo, P.; Kwok, W. M.; Chan, W. S.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. Time Resolved Resonance Raman Study of the Triplet States of p-Hydroxyacetophenone Molecule and the p-Hydroxyphenacyl Diethyl Phosphate Phototrigger Compound. J. Org. Chem. 2004, 69, 6641-6657. [PDF] [Supporting Info]

Edited Book Chapters and Reference Works:

36. Ou, J.; Toy, P. H. Organic Polymer Microencapsulated Metal Catalysts. In Recoverable and Recyclable Catalysts; Benaglia, M., Ed.; Wiley, 2009; pp 341-377.

37. But, T. Y. S.; Toy, P. H. Selenium- and Tellurium-Based Linker Units. In Linker Strategies in Solid-Phase Organic Synthesis; Scott, P. J. H., Ed.; Wiley, 2009. In press.

38. Toy, P. H. JandaJel. In Electronic Encyclopedia of Reagents in Organic Synthesis; Paquette, L. A., Fuchs, P. L., Wipf, P., Crich, D. C. Eds.; Wiley, 2004. [PDF]

39. Toy, P. H. Tentagel. In Electronic Encyclopedia of Reagents in Organic Synthesis; Paquette, L. A., Fuchs, P. L., Wipf, P., Crich, D. C. Eds.; Wiley, 2004. [PDF]

40. Toy, P. H. Polystyrene. In Electronic Encyclopedia of Reagents in Organic Synthesis; Paquette, L. A., Fuchs, P. L., Wipf, P., Crich, D. C. Eds.; Wiley, 2003. [PDF]

Wyeth Publication:

41. Gilbert, A. M.; Kirisits, M.; Toy, P.; Nunn, D. S.; Failli, A.; Dushin, E. G.; Novikova, E.; Petersen, P. J.; Joseph-McCarthy, D.; McFadyen, I.; Fritz, C. C. Anthranilate 4H-Oxazol-5-ones: Novel Small Molecule Antibacterial Acyl Carrier Protein Synthase (AcpS) Inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 37-41. [PDF]

Post-Doctoral Research Publications:

42. Toy, P. H.; Reger, T. S.; Garibay, P.; Garno, J. C.; Malikayil, J. A.; Liu, G.-Y.; Janda, K. D. Polytetrahydrofuran Cross-Linked Polystyrene Resins for Solid-Phase Organic Synthesis. J. Comb. Chem. 2001, 3, 117-124. [PDF] [Supporting Info]

43. Toy, P. H.; Reger, T. S.; Janda, K. D. Tailoring Polystyrene Solid-Phase Synthesis Resins: Incorporation of Flexible Cross-Linkers. Aldrichimica Acta. 2000, 33, 87-93. [PDF]

44. Toy, P. H.; Janda, K. D. Soluble Polymer-Supported Organic Synthesis. Acc. Chem. Res. 2000, 33, 546-554. [PDF]

45. Toy, P. H.; Reger, T. S.; Janda, K. D. Soluble Polymer Bound Cleavage Reagents: A Multipolymer Strategy for the Cleavage of Tertiary Amines from REM Resin. Org. Lett. 2000, 2, 2205-2207. [PDF] [Supporting Info]

46. Toy, P. H.; Janda, K. D. New Supports for Solid-Phase Synthesis: Development of Polystyrene Resins Containing Tetrahydrofuran Derived Cross-Linkers. Tetrahedron Lett. 1999, 40, 6329-6332. [PDF]

47. Garibay, P.; Toy, P. H.; Hoeg-Jensen, T.; Janda, K. D. Application of a New Solid–Phase Resin: Benzamide ortho-Lithiation and the Synthesis of a Phthalide Library. Synlett 1999, 1438-1440. [PDF]

Doctoral Studies Publications:

48. Newcomb, M.; Toy, P. H. Hypersensitive Radical Probes and the Mechanisms of Cytochrome P450-Catalyzed Hydroxylation Reactions. Acc. Chem. Res. 2000, 33, 449-455. [PDF]

49. Newcomb, M.; Shen, R.; Choi, S.-Y.; Toy, P. H.; Hollenberg, P. F.; Vaz, A. D. N.; Coon, M. J. Cytochrome P450-Catalyzed Hydroxylation of Mechanistic Probes that Distinguish Between Radicals and Cations. Evidence for Cations but Not for Radical Intermediates. J. Am. Chem. Soc. 2000, 122, 2677-2686. [PDF] [Supporting Info]

50. Newcomb, M.; Choi, S.-Y.; Toy, P. H. Picosecond Radical Kinetics. Rate Constants for Ring Openings of 2-Aryl-Substituted Cyclopropylcarbinyl Radicals. Can. J. Chem. 1999, 77, 1123-1135. [PDF]

51. Valentine, A. M.; Le Tadic-Biadatti, M.-H.; Toy, P. H.; Newcomb, M.; Lippard, S. J. Oxidation of Ultrafast Radical Clock Substrate Probes by the Soluble Methane Monooxygenase from Methylococcus capsulatus (Bath). J. Biol. Chem. 1999, 274, 10771-10776. [PDF]

52. Toy, P. H.; Newcomb, M.; Coon, M. J.; Vaz, A. D. N. Two Distinct Electrophilic Oxidants Effect Hydroxylation in Cytochrome P450-Catalyzed Reactions. J. Am. Chem. Soc. 1998, 120, 9718-9719. [PDF] [Supporting Info]

53. Toy, P. H.; Newcomb, M.; Hollenberg, P. F. Hypersensitive Mechanistic Probe Studies of Cytochrome P450-Catalyzed Hydroxylation Reactions. Implications for the Cationic Pathway. J. Am. Chem. Soc. 1998, 120, 7719-7729. [PDF] [Supporting Info]

54. Choi, S.-Y.; Toy, P. H.; Newcomb, M. Picosecond Radical Kinetics. Fast Ring Openings of Secondary and Tertiary trans-2-Phenylcyclopropylcarbinyl Radicals. J. Org. Chem. 1998, 63, 8609-8613. [PDF] [Supporting Info]

55. Toy, P. H.; Newcomb, M.; Hager, L. P. Hypersensitive Mechanistic Probe Studies of Chloroperoxidase-Catalyzed Hydroxylation Reactions. Chem. Res. Toxicol. 1998, 11, 816-823. [PDF]

56. Toy, P. H.; Dhanabalasingam, B.; Newcomb, M.; Hanna, I. H.; Hollenberg, P. F. A Substituted Hypersensitive Radical Probe for Enzyme-Catalyzed Hydroxylations: Synthesis of Racemic and Enantiomerically Enriched Forms and Application in a Cytochrome P450-Catalyzed Oxidation. J. Org. Chem. 1997, 62, 9114-9122. [PDF] [Supporting Info]

July 11, 2006: Keio University, Yokohama, Japan

Our Research Group (Oct. 2009):
L to R: Hong Yau Hin Eugene (undergraduate, project student), Ou Jun Jack (PGS),
Julia Hermeke (PGS), Leung Shu Wai Peter (PGS), Dr. Toy, Law Chun Hin Henry (undergraduate, project student),
Lu Jinni Jean (PGS), Teng Yan Jackie (PGS)