Protecing-Group-Free Synthesis. Reporter: Zhu Zhiyang Advisor: Prof Yang Prof Chen Prof Tang Date:
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1 Protecing-Group-Free Synthesis Reporter: Zhu Zhiyang Advisor: Prof Yang Prof Chen Prof Tang Date:
2 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples Metal-mediated reaction Cascade reaction Biomimetic & nature-inspired synthesis Other reaction path Flow-microreactor approach Summary Acknowledgement 2
3 Introduction Organic Synthesis Step- Solvents take money? Atom- Redox- Economy Green Chemistry Can we synthesize it? How can we synthesize it? Protecting-Group-Free Synthesis 3
4 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples Metal-mediated reaction Cascade reaction Biomimetic & nature-inspired synthesis Other reaction path Flow-microreactor approach Summary Acknowledgement 4
5 Historic Background early stage R. Robinson, Jan 1 st 1917 Conducted on gram scale Characterized by elemental analysis & melting point Protecting-group-free synthesis 5
6 Historic Background Intermediate time S. Danishefsky, 1968 R. V. Stevens, 1983 & C. H. Heathcock, 1993 Danishefsky, S. & Dumas, D. Chem. Commun (1968). Stevens, R. V. & Kenney, P. M. J. Chem.Soc. Chem. Commun (1983). Stoermer, D. & Heathcock, C. H.. J. Org. Chem. 58, (1993). 6
7 Historic Background Invention-oriented PGF synthesis P. S. Baran, 2004 first instances of deliberately avoid protecting groups through synthetic design Baran, P. S. & Richter, J. M. J. Am. Chem. Soc. 126, (2004). 7
8 Historic Background Invention-oriented PGF synthesis P. S. Baran, 2005 & 2007 Baran, P. S. & Richter, J. M. J. Am. Chem. Soc. 127, (2005). Baran, P. S., Maimone, T. J. & Richter, J. M. Nature 446, (2007). 8
9 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples Metal-mediated reaction Cascade reaction Biomimetic & nature-inspired synthesis Other reaction path Flow-microreactor approach Summary Acknowledgement 9
10 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples Metal-mediated reaction Cascade reaction Biomimetic & nature-inspired synthesis Other reaction path Flow-microreactor approach Summary Acknowledgement 10
11 Strategies & examples - Metal-mediated reaction S. Kobayashi, 2012 P. S. Baran, 2012 B. M. Stoltz, 2008 Fujita, K.; Matsui, R.; Suzuki, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2012, 51, Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51, Enquist, J. A. & Stoltz, B. M. Nature 453, (2008). 11
12 Strategies & examples - Metal-mediated cross coupling S. Kobayashi, Metal-mediated cross coupling Fujita, K.; Matsui, R.; Suzuki, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2012, 51,
13 Strategies & examples - Metal-mediated cross coupling S. Kobayashi, Metal-mediated cross coupling Fujita, K.; Matsui, R.; Suzuki, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2012, 51,
14 Strategies & examples - Metal-mediated C-H activation P. S. Baran, Metal-mediated C-H activation Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51,
15 Strategies & examples - Metal-mediated C-H activation P. S. Baran, Metal-mediated C-H activation Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51,
16 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples Metal-mediated reaction Cascade reaction Biomimetic & nature-inspired synthesis Other reaction path Flow-microreactor approach Summary Acknowledgement 16
17 Strategies & examples - Cascade reaction Ma Dawei, Cascade reaction Zhou, Q.; Chen, X.; Ma, D. Angew. Chem.,Int. Ed. 2010, 49,
18 Strategies & examples - Cascade reaction Ma Dawei, Cascade reaction Zhou, Q.; Chen, X.; Ma, D. Angew. Chem.,Int. Ed. 2010, 49,
19 Strategies & examples - Cascade reaction Ma Dawei, Cascade reaction Zhou, Q.; Chen, X.; Ma, D. Angew. Chem.,Int. Ed. 2010, 49,
20 Strategies & examples - Cascade reaction F. Ridriguez, Cascade reaction Fananas, F. J.; Mendoza, A.; Arto, T.; Temelli, B.; Ridriguez, F. Angew. Chem., Int. Ed. 2012, 51,
21 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples Metal-mediated reaction Cascade reaction Biomimetic & nature-inspired synthesis Other reaction path Flow-microreactor approach Summary Acknowledgement 21
22 Strategies & examples - Biomimetic pericyclic reaction D. Trauner, 2005 Lumb, J.; Trauner, D. J. Am. Chem.Soc. 2005, 127,
23 Strategies & examples - Biomimetic pericyclic reaction Lumb, J.; Trauner, D. J. Am. Chem.Soc. 2005, 127,
24 Strategies & examples Nature-inspired rearrangement E. A. Theodorakis, 2012 Xu, J.; Caro-Diaz, J. E.; Trzoss, L.; Theodorakis, E. A. J. Am. Chem. Soc. 2012, 134,
25 Strategies & examples - Nature-inspired rearrangement E. A. Theodorakis, 2012 Xu, J.; Caro-Diaz, J. E.; Trzoss, L.; Theodorakis, E. A. J. Am. Chem. Soc. 2012, 134,
26 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples Metal-mediated reaction Cascade reaction Biomimetic & nature-inspired synthesis Other reaction path Flow-microreactor approach Summary Acknowledgement 26
27 Strategies & examples - Other reaction path Yao Zhujun, 2012 Ge, H. M.; Zhang, L.-D.; Tan, R. X.; Jao, Z. J. J. Am. Chem. Soc. 2012, 134,
28 Strategies & examples - Other reaction path Yao Zhujun, 2012 Ge, H. M.; Zhang, L.-D.; Tan, R. X.; Jao, Z. J. J. Am. Chem. Soc. 2012, 134,
29 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples Metal-mediated reaction Cascade reaction Biomimetic & nature-inspired synthesis Other reaction path Flow-microreactor approach Summary Acknowledgement 29
30 Strategies & examples - Flow-microreactor approach J. Yoshida, 2011 H. Kim, A. Nagaki, J. Yoshida, Nat. Commun. 2011, 2,
31 Strategies & examples - Flow-microreactor approach Substrate scope H. Kim, A. Nagaki, J. Yoshida, Nat. Commun. 2011, 2,
32 Strategies & examples - Flow-microreactor approach J. Yoshida, 2011 H. Kim, A. Nagaki, J. Yoshida, Nat. Commun. 2011, 2,
33 Summary Metal-mediated reaction Cascade reaction Biomimetic & nature-inspired synthesis Other reaction path Flow-microreactor approach We are creating art rather than just making molecules! 33
34 Acknowledgement Prof. Yang, Prof. Chen & Prof. Tang Mr. You Lin, Mr. Liang Xinting, Mr Li Yuanhe, Mr Zhang Wei Mr. Tong Bingqi Everyone here 34
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