个人简介

Ph.D. (2003) UC DAVIS Postdoctoral Fellow: The Scripps Research Institute /Oxford University (2005-2007) Stanford University (2003-2005)

研究领域

Organic synthesis, materials

Organic materials based on pi-extended porphyrins The challenge from energy increasingly demands new functional materials to convert solar energy to electricity or chemical fuels in high efficiency. Currently, there is a request for materials that can effectively harvesting solar energy in the red and near IR region. Extended porphyrins (porphyrins fused with aromatic rings) are of broad interest due to their unique combination of photophysical, optoelectronic, and physicochemical properties, and their potential applications in many areas. While porphyrins have been studied for decades, extended porphyrins remain largely unexplored due to the very limited synthetic methods, in particular, the marked lack of methods for the functionalization of their periphery extremely limiting their possible structures. This synthetic limitation makes the design and synthesis of extended porphyrins very challenging. We are engaged in two research activities: The development of concise and versatile methodologies to access a large number of pi-extended porphyrins. The design and development of new organic materials based on these functionalized pi-extended porphyrins for electronic applications and solar energy conversion. Enamine-metal Lewis acid bifunctional catalysis The rapid growth of biological science, materials science, and the pharmaceutical industry has placed increasing demand for chiral materials with structural complexity. Asymmetric catalysis is the most efficient and atom-economic approaches to building up stereochemical complexity. The development of novel catalytic systems for asymmetric transformations has remained a long-lasting interest. The combination of organocatalysis with metal catalysis has just emerged as a potentially powerful tool in organic synthesis. This new concept aims to deliver new organic transformations that cannot be accomplished by organocatalysis or metal catalysis independently. This area offers huge potential for the discovery of new carbon-carbon and carbon-hetero-atom bond forming reactions, and remains largely unexplored. In the longer term, we are interested in developing efficient approaches to the combination of all types of organocatalysis with metal catalysis. At the first stage, our focus is on the integration of organo-enamine catalysis with metal Lewis acid catalysis. In the development of enamine-metal Lewis acid bifunctional catalysts, we address three issues: The combination of enamine catalysis with strong metal Lewis acid catalysis. One of the weaknesses of the organocatalysts is their relatively low catalytic activity. In organo-enamine catalysis, it is generally accepted that a chiral amine, often L-proline or its derivatives, forms an enamine nucleophile, raising the HOMO of an aldehyde or a ketone. The electrophile is activated through hydrogen bonding. We use a stronger Lewis acid instead of the hydrogen-bonding activation in order to attain much higher activation of the enamine acceptors. In addition, by using an intramolecular bifunctional catalyst, an intermolecular reaction can be converted into a much more efficient intramolecular reaction. In this way, we aim to develop highly active catalysts to extend the substrate scope of the organocatalytic reactions and to achieve difficult organic transformations. The incorporation of a chiral amine in the catalysts to attain high stereoselectivity of the asymmetric organic reactions. This feature can again be enhanced by the intramolecular bifunctional nature of the catalysts. The combination of a large variety of metal catalysis with enamine catalysis so that more extensive investigation of this area can be carried out in the long term. The development of small molecule inhibitors targeting STAT3 as potential therapeutic agents Signal transducer and activator of transcription 3 (STAT3) is a transcription factor belonging to a family of seven (STATs) proteins that regulate important cellular processes such as cell survival, immune response, angiogenesis and cell proliferation. Activation of STAT3 stimulates the growth of tumor cells, and confers resistance to conventional therapies. The development of small molecule inhibitors targeting STAT3 has remained an intense research interest in recent years. Very recently, we have discovered a novel class of small organic molecules that have shown to inhibit STAT3 phosphorylation and cause apoptosis in human hepatocellular carcinoma cells. The goal of this project is to modify the structures of these inhibitors to achieve high cell affinity and high inhibitory activity.

近期论文

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Y. Deng, S. Kumar, K. Wheeler, H. Wang,* “Trio Catalysis Merging Enamine, Brønsted Acid and Metal Lewis Acid Catalysis: Asymmetric Three-Component Aza-Diels Alder Reaction of Substituted Cinnamaldehydes, Cyclic ketones, and Arylamines”, submitted. P. Daka, A. Liu, E. Csatary, C. Williams,J. Lin,R. Page,* H. Wang,*“Design, synthesis and evaluation of XZH-5 analogues as STAT3 inhibitors”, Submitted. Y. Deng, E. Castary, K. Wheeler, D. L. Tierney,H. Wang,* “Lewis Acid Assisted Lewis Acid Catalysts Derived from Metal Lewis Acids and Chiral Metal Phosphates: Three-Component Asymmetric ADARs of Cyclic Ketones”, submitted. L. Jiang,J. T. Engle,R. A. Zaenglein,A. Matus,C. J. Ziegler,H. Wang,* M. J. Stillman,* “Pentacene-Fused Diporphyrins”, Chem. Eur. J. 2014, 20, 1-7. Selected as a “hot paper”. L. Liu, P.Daka, R. Sarkisian, Y. Deng, K. Wheeler, H. Wang* “Oxa-Diels–Alder Reaction of Isatins and Acyclic ß,ß-Unsaturated MethylKetones through Cooperative Dienamine and Metal Lewis Acid Catalysis”, Synthesis, 2014, 1339-1347. Invited article to a special issues of Synthesis featuring synergistic use of organo- and metal catalysis. Y. Deng, S. Kumar, H. Wang,* “Merging Organoamino Catalysis with Metal Lewis Acid Catalysis”, invited feature article to Chem. Commun., 2014, 4272-4284. X. Wang, S. Dong, Z. Yao, L. Feng, P. Daka,H. Wangand Z. Xu,*“Synthesis of Spiroaminals and Spiroketals with Tandem Metal Relay Catalysis”, Org. Lett.,2014, 16(1), 22-25. Lu Liu, Ryan Sarkisian, Yongming Deng, Hong Wang*, "Sc(OTf)3-Catalyzed Three-Component Cyclization of Arylamines, beta, gamma-Unsaturated alpha-Ketoesters and 1,3-Dicarbonyl Compounds for The Synthesis of highly Substituted 1,4-Dihydropyridines and Tetrahydropyridines", accepted to J. Org. Chem. Xianghua Wang, Zhili Yao, Shuili Dong, Fang Wei, Hong Wang, Zhenghu Xu*, “Synthesis of Fused Bicyclic Aminals through Sequential Gold / Lewis Acid Catalysis”, accepted to Org. Lett. Yongming Deng, Lu Liu, Ryan G. Sarkisian, Kraig Wheeler, Hong Wang* and Zhenghu Xu*, "Arylamine-Catalyzed Enamine Formation: Cooperative Catalysis with Arylamines and Acid", Angew. Chem. Int. Ed. 2013, 52, 3663–3667. Highlighted in SYNFACT issue 06/13. Rohit Deshpande, Bo Wang, Lin Dai, Scott Hartley, Shouzhong Zou, Hong Wang,* Lei Kerr,* “opp-Dibenzoporphyrins as light harvesters for dye-sensitized-solar cells”, accepted to Chem. Asian J. 2012, 7, 2662-2669. Aiguo Liu; Yan Liu; Li Lin; Zhenghu Xu; Hong Wang; Chenglong Li; Jiayuh Li*, 2012; 7(10): e46624. Lu Liu, Ryan Sarkisian, Zhenghu Xu, Hong Wang*, “Asymmetric Michael additions through Enamine-mteal Lewis acid byfunctional catalysts”, accepted to J. Org. Chem. 2012, 77, 7693-7699. L. Jiang, R. A. Zaenglein, J. T. Engle, C. Mittal, C. S. Hartley, C. J. Ziegler, and H. Wang*, “Water-soluble ionic benzoporphyrins”, Chem Commun, 2012, 6927-6929. Invited contribution to a themed issue featuring Porphyrins & Phthalocyanines. Zhenghu Xu, Hong Wang, "Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction of Ketones", invited SYNPACT paper, accepted to Synlett. L. Jiang, J. T. Engle, L. Sirk, C. S. Hartley, C. J. Ziegler, and H. Wang*, "Triphenylene-fused Porphyrins", Org. Lett., 2011, 13, 3020-3023. A. Liu, Y. Liu, Z. Xu, W. Yu, H. Wang, C. Li, J. Lin, "A Novel Small Molecule, XZH-5, Inhibits Constitutive and Interleukin-6-Induced STAT3 Phosphorylation in Human Rhabdomyosarcoma Cells", Cancer Science, 2011, 102, 1381-1387 Highlighted in Cancer Science.vol.102 iss.7. Y. Liu, A. Liu, Z. Xu, W. Yu, H. Wang, C. Li, J. Lin, "XZH-5 Inhibits STAT3 Phosphorylation and Causes Apoptosis in Human Hepatocellular Carcinoma Cells", Apoptosis, 2011, 16, 502-510. Z. Hu, K. Wheeler, H. Wang*, "Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction of Cyclic Ketones: An Enamine-Metal Lewis Acid Bifunctional Approach", Angew. Chem. Int. Ed. 2011, 50, 3484-3488. Chosen as a "Hot Paper" by the Editors for its importance in a rapidly evovling field of high current interest. Highlighted in SYNFACTS issue 07/11. P. Daka, Z. Xu, A. Alexa, H. Wang*, " Primary amine-metal Lewis acid bifunctional catalysts based on a simple bidentate ligand: direct asymmetric aldol reaction", Chem. Commun. 2011,47, 224-226. invited paper, issue of Emerging New Investigator. Higlighted in SYNFACT, issue 4/10/2011.