题 目：Reengineering Classic Organic Reactions

时 间：2014年3月10日下午14:00-15:30

地 点：四方校区1教206

主讲人：香港大学Patrick H. Toy 教授

内容摘要：

Many well-known reactions are commonly used in organic synthesis even though they often suffer from serious operational difficulties. For example, the Mitsunobu and Wittig reactions both produce stoichiometric quantities of by-products that can complicate isolation of the desired product. Thus, a long-standing theme of our research has been to use polymer-supported reagents to facilitate the execution of such reactions. This research inspired us to design new ways for performing these classic organic reactions so that they can be applied in new contexts. Originally, the Mitsunobu reaction was studied extensively, followed by the Wittig reaction. More recently we have extended our research to aza-Wittig reactions that are analogous to reductive amination transformations, and palladium-catalysed cross-coupling reactions such as the Suzuki, Sonagashira and Heck reactions. Highlights of this research will be presented during this seminar.

主讲人简历：

Patrick H. Toy

Associate Professor

Department of Chemistry

Universityof Hong Kong

Hong Kong, People’s Republic of China

Areas of Specialization: Organic, Combinatorial and Polymer Chemistry

Research Interests: Polymers in organic chemistry, organocatalysis of Mitsunobu, Morita-Baylis-Hillman, and alkyne rearrangement reactions, organoarsine chemistry, polymers for water purification applications.

Education:

1. B.S., Ohio State University (6/1990)

2. Ph.D., Wayne State University (5/1998)

Professional Positions:

1. Department of Chemistry, Scripps Research Institute, Post-Doctoral Research Associate, Research Supervisor: Prof. Kim D. Janda (6/1998 – 6/2000)

2. Department of Combinatorial Chemistry, Wyeth (now a part of Pfizer), Research Scientist, Supervisor: Dr. John Ellingboe (7/2000 – 9/2001)

3. Department of Chemistry, University of Hong Kong, Assistant Professor (10/2001 – 5/2007)

4. Department of Chemistry, University of Hong Kong, Associate Professor (6/2007 – present)

Representative Peer Reviewed Journal Publications:

1. Andrew M. Harned, Helen Song He, Patrick H. Toy, Daniel L. Flynn and Paul R. Hanson, Multipolymer Solution-Phase Reactions: Application to the Mitsunobu Reaction. J. Am. Chem. Soc. 2005, 127, 52-53.

2. Tracy Yuen-Sze But and Patrick H Toy, Organocatalytic Mitsunobu Reactions. J. Am. Chem. Soc. 2006, 128, 9636-9637.

3. Cathy Kar-Wing Kwong, Rui Huang, Minjuan Zhang, Min Shi and Patrick H. Toy, Bifunctional Polymeric Organocatalysts and Their Application in the Cooperative Catalysis of Morita-Baylis-Hillman Reactions. Chem. Eur. J. 2007, 13, 2369-2376.

4. Jinni Lu and Patrick H. Toy, Organic Polymer Supports for Synthesis and for Reagent and Catalyst Immobilization. Chem. Rev. 2009, 109, 815-838.

5. Cathy Kar-Wing Kwong, Michael Yunyi Fu, Henry Chun-Hin Law and Patrick H. Toy, Isomerization of Electron-Poor Alkynes to the Corresponding (E,E)-1,3-Dienes Using a Bifunctional Polymeric Catalyst Bearing Triphenylphosphine and Phenol Groups. Synlett 2010, 2617-2620.

6. Peter Shu-Wai Leung, Yan Teng and Patrick H. Toy, Chromatography-Free Wittig Reactions Using a Bifunctional Polymeric Reagent. Org. Lett. 2010, 12, 4996-4999.

7. Julia Hermeke and Patrick H. Toy, Phosphonium Ion Tagged Chiral Phosphoric Acids and Their Application in Friedel-Crafts Reactions of Indoles. Tetrahedron 2011, 67, 4103-4109.

8. Jinni Lu and Patrick H. Toy, Tandem One-Pot Wittig/Reductive Aldol Condensation Reactions in which the Waste from One Process Catalyzes a Subsequent Reaction. Chem. Asian J. 2011, 6, 2251-2254.

9. Yan Teng, Jinni Lu, and Patrick H. Toy, Rasta Resin-PPh3-NBniPr2 and its Use in One-Pot Wittig Reaction Cascades. Chem. Asian J. 2012, 7, 351-359.

10. Bo Wu, Kun Li and Patrick H. Toy, Synthesis of Hydroxy--Sanshool. Synlett 2012, 2564-2566.