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李志平 教授
 

 

 

Welcome to Prof. Zhiping Li’s group

 

Address 

Prof. Zhiping Li                                          

Department of Chemistry

Renmin University of China

Beijing 100872, China

Telephone: +86-10-6251-4226

Fax: +86-10-6251-6444

E-mail: zhipingli@ruc.edu.cn

 

Education

 

B.Sc.: Nanjing University of Science and Technology, 1989-1993

M. Sc.: Nanjing University of Science and Technology, 1993-1995 (with Professors Chunxu Lv and Yunyang Wei)

Ph.D.: Dalian University of Technology, 1996-1999 (with Professors Xigao Jian and Guodu Ren)

Postdoctoral Fellow: Peking University, 1999-2000 (with Professor Zhenfeng Xi)

Postdoctoral Fellow: Hokkaido University, Japan, 2001-2002 (with Professor Tamotsu Takahashi)

Postdoctoral Fellow: McGill University, Canada, 2004-2006 (with Professor Chao-Jun Li)

 

Acdemic career

 

Assistant Professor: Peking University, 2002.8-2003.12

Associate Professor: Renmin University of China, 2006.3-2009.8

Professor: Renmin University of China, 2009.9-now

 

Qualifications and awards

 

1.      New Century Excellent Talents in University (2007)

2.      Technology Innovation of Pioneer Capital Education (2009)

 

Selected publications

1.  Xingwei Guo, Rong Yu, Haijun Li, and Zhiping Li*. Iron-Catalyzed Tandem Oxidative Coupling and Annulation: An Efficient Approach to Construct Polysubstituted Benzofurans. J. Am. Chem. Soc. 2009, 131, 17387–17393.

2.  Xingwei Guo, Shiguang Pan, Jinhua Liu, and Zhiping Li*. One-Pot Synthesis of Symmetric and Unsymmetric 1,1-Bis-indolylmethanes via Tandem Iron-Catalyzed C-H Bond Oxidation and C-O Bond Cleavage. J. Org. Chem. 2009, 74, 8848–8851.

3.   Xingwei Guo, Shiguang Pan, Jinhua Liu, and Zhiping Li*. One-Pot Synthesis of Symmetric and Unsymmetric 1,1-Bis-methyl amines: highly efficient synthesis of methylene-bridged bis-1,3-dicarbonyl compounds. Org. Lett., 2009, 11, 4176–4179.

4.   Haijun Li, Wenjuan Li, Zhiping Li*. Iron-catalyzed cross-aldol reactions of ortho-diketones and methyl ketones. Chem. Commun. 2009, 3264-3266.

5.      Zhiping Li*, Rong Yu, Haijun Li. Iron-catalyzed C-C bond formation by direct functionalization of C-H bonds adjacent to heteroatoms Angew. Chem. Int. Ed. 2008, 47, 7497-7500.

6.      Zhiping Li*, Haijun Li, Xingwei Guo, Lin Cao, Rong Yu, Huanrong Li, and Shiguang Pan. C-H Bond oxidation initiated Pummerer- and Knoevenagel-type reactions of benzyl sulfide and 1,3-dicarbonyl compounds. Org. Lett. 2008, 10, 803-805.

7.      Zhiping Li*, Lin Cao, Chao-Jun Li*. FeCl2-catalyzed selective C-C bond formation by oxidative activation of a benzylic C-H bond. Angew. Chem. Int. Ed. 2007, 46, 6505-6507.

8.      Zhiping Li, D. Scott Bohle, and Chao-Jun Li*. Cu-catalyzed cross-dehydrogenative coupling: A versatile strategy for C–C bond formations via the oxidative activation of sp3 C–H bonds. Proc. Natl. Acad. Sci. USA, 2006, 103, 8928-8933.

9.      Zhiping Li, and Chao-Jun Li*. Catalytic Allylic Alkylation via the Cross-Dehydrogenative-Coupling (CDC) Reaction between Allylic sp3 C-H and Methylenic sp3 C-H Bonds. J. Am. Chem. Soc. 2006, 128, 56-57.

10.      Zhiping Li, and Chao-Jun Li*. CuBr-Catalyzed Direct Indolation of Tetrahydroisoquinolines via Cross-Dehydrogenative Coupling between sp3 C-H and sp2 C-H Bonds. J. Am. Chem. Soc. 2005, 127, 6968-6969.

11.      Zhiping Li, and Chao-Jun Li*. Highly Efficient Copper-Catalyzed Nitro-Mannich Type Reaction: Cross-Dehydrogenative- Coupling (CDC) between sp3 C-H Bond and sp3 C-H Bond. J. Am. Chem. Soc. 2005, 127, 3672-3673.

12.  Zhiping Li, and Chao-Jun Li*. Catalytic Enantioselective Alkynylation of Prochiral sp3 C-H Bonds Adjacent to a Nitrogen Atom. Org. Lett. 2004, 6, 4997-4999.

13.  Zhiping Li, and Chao-Jun Li*. CuBr-catalyzed Efficient Alkynylation of sp3 C-H Bonds Adjacent to a Nitrogen Atom. J. Am. Chem. Soc. 2004, 126, 11810-11811.

14.  Xin Zhou, Zhiping Li, Hui Wang, Masanori Kitamura, Ken-ichiro Kanno, Kiyohiko Nakajima, and Tamotsu Takahashi*. Novel Synthetic Route to Octasubstituted Naphthalenes from Four Alkynes and One Olefin Unit via Zirconacyclopentadienes and 1,2-Diiodo-3,4,5,6- tetraalkylbenzene. J. Org. Chem. 2004, 69, 4559-4562.

15.  Xiaohua Sun, Congyang Wang, Zhiping Li, Shiwei Zhang, and Zhenfeng Xi*. Zirconocene-Mediated Intermolecular Coupling of One Molecule of Si-Tethered Diyne with Three Molecules of Organonitriles: One-Pot Formation of Pyrrolo[3,2-c]pyridine Derivatives via Cleavage of CºN Triple Bonds of Organonitriles. J. Am. Chem. Soc. 2004, 126 (23), 7172-7173.

Research interests

 

Dr. Zhiping’s group is current focusing on seeking novel synthetic methodologies based on the selective oxidation of C-H bonds (Scheme 1). 

(1)   Iron-catalyzed C-H bond oxidation directed towards organic synthesis

The applications of inexpensive, easily available and nontoxic iron catalysts are attracting great attention in organic chemistry. Iron catalysts are well-known catalysts in C-H bonds oxidation, wherein C-O bonds and C-X bonds were formed. Inspired by nature and previous excellent results, we rationalized that it would be an efficient method of C-C bond formation by direct and selective C-H bond oxidation. Here are some of our recent results toward this idea, including benzylic C-H bond oxidation, α-heteroatom C-H bond oxidation and aromatic C-H bond oxidation (Scheme 2). Iron catalysts together with organic peroxide have been proved to be very efficient in oxidative C-H bond activation and C-C bond formation.

(2)   Molecular iodine-mediated C-H bond oxidation in organic synthesis

Metal-free syntheses are highly attractive in synthetic chemistry, especially in pharmaceutical synthesis. The low cast and less toxicity molecular iodine is one of environmentally benign reagents and was broadly used in organic synthesis. Our efforts in the development of novel methodologies for organic synthesis promoted us to investigate molecular iodine-mediated C-H bond oxidation and C-C bond formation. Indole derivatives are the biologically important natural products. Many efforts have been made to achieve the synthesis of this motif. Various innovative and powerful methodologies for the synthesis of indole derivatives have been developed. With our efforts, an efficient and practical synthesis of indole and its derivatives was achieved via I2-mediated oxidative coupling reactions without sacrificed organic functional groups (Scheme 3).

(3)   The application of o-chloranil in C-C bond formation

C-C bond formation is an important research topic in organic synthesis. Various methodologies are developed toward this target. As one of the fundamental innovations in organic chemistry, “chemistry beyond functional group transformation”, which uses readily available, cheap and non-toxic materials to construct targeted molecules with high yields under mild conditions, is highly desired.

o-Chloranil (tetrachloro-o-benzoquinone) is usually used as an oxidant in oxidation reactions. During our studies, o-chloranil was applied efficiently in C-C bond formation. Two types of C-C bond formation using o-chloranil will be discussed: (1) a novel Pummerer-type reaction is developed via o-chloranil-mediated C-H bond oxidation. The reaction presents a simple and efficient method to construct sulfide derivatives. Interestingly, the Knoevenagel-type reaction is selectively achieved by controlled reaction conditions (Eq.1); (2) efficient iron-catalyzed cross-aldol reactions of o-chloranil and methyl ketones are developed. Importantly, the formed aldol products are efficiently transformed into cyclohepta-2,4,6-trienone derivatives (tropones) under thermal condition via ring-expansion reactions (Eq.2). Further ring-contraction reactions of tropone derivatives is also interesting (Eq.3).


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