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Boshun Wan ( 万伯顺 ) E-mail: bswan@dicp.ac

Recent Advances for the Selective Synthesis of Heterocycles. Boshun Wan ( 万伯顺 ) E-mail: bswan@dicp.ac.cn. Heterocycles for Sustainable Chemistry. Natural products. Pharmaceuticals. Heterocycles. Chemicals for R&D. Polymer Materials. Top 100 Brand Name Drugs by US Retail Sales in 2010.

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Boshun Wan ( 万伯顺 ) E-mail: bswan@dicp.ac

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  1. Recent Advances for the Selective Synthesis of Heterocycles Boshun Wan (万伯顺) E-mail: bswan@dicp.ac.cn

  2. Heterocycles for Sustainable Chemistry Natural products Pharmaceuticals Heterocycles Chemicals for R&D Polymer Materials

  3. Top 100 Brand Name Drugs by US Retail Sales in 2010 Heterocycles: ~50%; Pyridine/Pyrrole: ~10% http://cbc.arizona.edu/njardarson/group/top-pharmaceuticals-poster

  4. Overview of My Group

  5. Why Cycloadditon?

  6. Developed Catalytic Systems Louie, J. Saá, C. Vollhardt Takahashi, T. “CpCo” “Ni/NHC” “Zr/Ni” Generic description of the 6 factors Metal-catalyzed [2 + 2 + 2] cycloaddition Urabe, H. Tanaka, K. “Ti(OiPr)4/iPrMgCl” “Rh/P-P” Yamamoto, Y. Guerchais, V. Saá, C. Zenneck, U. “Cp*Ru” “Fe(0)” “Fe(+I)” (a) Varela, J. A.; Saá, C. Chem. Rev. 2003, 103, 3787. (b) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307. (c) Heller, B.; Hapke, M. Chem. Soc. Rev. 2007, 36, 1085. (d) Varela, J. A.; Saá, C. Synlett2008, 2571. (e) Wang, C. X.; Li, X. C.; Xu, F.; Wan, B. S. Prog. Chem. 2010, 22, 610.

  7. Why Iron? US$ per mol Iron(I) complex 2011 Iron(0) complex Iron (0.02 US$/mol)

  8. Iron Catalytic System

  9. Problems and Solutions Three crucial problems: 1. Low-valent metal 2. Substrate Coordination & Product Dissociation 3. Benzene byproducts

  10. Problems and Solutions

  11. Cycloaddition of Diynes and Unactivated Nitriles

  12. Cycloaddition of Diynes and Unactivated Nitriles (Continued)

  13. Cycloaddition of Tetrayne All-intramolecular Cycloaddition

  14. Cycloaddition of Alkynenitrile and Alkyne Louie, J.

  15. Control Experiments

  16. Possible Pathways to Form Pyridines

  17. Iron-Catalyzed Cycloaddition With Wang, C. X.Angew. Chem. Int. Ed. 2011, 50, 7162

  18. Cycloaddition of Alkynes and Nitriles in Water

  19. Ruthenium-catalyzed [2+2+2] Cycloaddition in Pure Water WithXu, F.ChemSusChem. 2012, 5, 854 (IF 6.325)

  20. Synthesis of Pyrroles via Cyclization

  21. Synthesis of Pyrroles via Cyclization

  22. Mechanism Study "α" Migration

  23. Mechanism Study Crossover Experiment anticipated products new products

  24. Mechanism Study "β" Migration

  25. Crossover Experiment Competition Experiment

  26. Highly Regioselective Sulfonyl-Group Migration Reactions With Xin, X. Y.Angew. Chem. Int. Ed. 2012, 51, 1693.

  27. Summary

  28. 苯并恶唑与不同磺酰肼的氧化偶联

  29. 苯并恶唑与不同磺酰肼的氧化偶联

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