Ruthenium(II)-Catalyzed C H Bond Activation and Functionalization
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1 Ruthenium(II)-Catalyzed C H Bond Activation and Functionalization Dixneuf, et al. Chem. Rev. 2012, 112, Dr. Fanyang Mo The Dong Group Dec. 12,
2 Why Ruthenium??? Reason 1: Previous group seminar topics. Metal Pd Rh Ir Presenter Zack, Tao and Momo Alpay, Huang, Rachel, Brandon and Momo Wallace, Hayemin and Momo Reason 2: The papers we have published. Metal Pd Rh Papers published 1 JACS and 1 ACIE 2 JACS and 1 ACIE 2
3 The price for metals on Dec. 7 th, 2012 USD/oz Source: 3
4 The price for metals on Dec. 7, 2012 USD / mmol Cobalt??? 10.7 USD / lb 0 < Source: 4
5 Contents 1. Ru(0) catalyzed C H activation (briefly) 2. Ru(II) catalyzed C H activation Arylation Allylation Alkylation Acylation Alkenylation Others Of (Hetero)Arenes and Alkene 3. Summary 4. Acknowledgement 5
6 Four different mechanisms for C H activation Question 1 Low valent latetransition-metals Early transition metals High valent latetransition-metals High valent latetransition-metals 6
7 Ru(0) catalyzed C H activation (1, 2, 3, 4) 1. Seminal paper Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366,
8 Ru(0) catalyzed C H activation 2. Catalysts prefer their own directing group. Kakiuchi, F.; Sato, T.; Tsujimoto, T.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1998, 27,
9 Ru(0) catalyzed C H activation 3. Alkynes also work a) Kakiuchi, F.; Uetsuhara, T.; Tanaka, Y.; Chatani, N.; Murai, S. J. Mol. Catal. A: Chem. 2002, 182, 511. b) Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, How to generate Ru(0) 9
10 1) Arylation The first example was reported by Oi and Inoue in Using aryl halides as both arylation reagents and oxidants. Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3,
11 1) Arylation Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3,
12 1) Arylation Oi, S.; Ogino, Y.; Fukita, S.; Inoue, Y. Org. Lett. 2002, 4,
13 1) Arylation Oi, S.; Sakai, K.; Inoue, Y. Org. Lett. 2005, 7,
14 1) Arylation Oi, S.; Sasamoto, H.; Funayama, R.; Inoue, Y. Chem. Lett. 2008, 37,
15 1) Arylation Oi, S.; Funayama, R.; Hattori, T.; Inoue, Y. Tetrahedron 2008, 64,
16 1) Arylation Ackermann, L. Org. Lett. 2005, 7,
17 1) Arylation Ackermann, L.; Pospech, J.; Potukuchi, H. K. Org. Lett. 2012, 14,
18 1) Arylation Ackermann, L.; Born, R.; Alvarez-Bercedo, P. Angew. Chem., Int. Ed. 2007, 46,
19 1) Arylation (a) Ackermann, L.; Althammer, A.; Born, R. Tetrahedron 2008, 64, (b) Ackermann, L.; Althammer, A.; Born, R. Synlett 2007,
20 1) Arylation---Mechanistic studies Fernandez, S.; Pfeffer, M.; Ritleng, V.; Sirlin, C. Organometallics 1999, 18, Dixneuf, P. H. and et al. J. Am. Chem. Soc. 2008, 130,
21 2) Allylation Oi, S.; Tanaka, Y.; Inoue, Y. Organometallics 2006, 25,
22 2) Allylation 22 Onodera, G.; Imajima, H.; Yamanashi, M.; Nishibayashi, Y.; Hidai, M.; Uemura, S. Organometallics 2004, 23, 5841.
23 3) Alkylation with alkenes Foley, N. A.; Lail, M.; Lee, J. P.; Gunnoe, T. B.; Cundari, T. R.; Petersen, J. L. J. Am. Chem. Soc. 2007, 129,
24 3) Alkylation with alkenes Youn, S. W.; Pastine, S. J.; Sames, D. Org. Lett. 2004, 6,
25 3) Alkylation with alkylhalides Ackermann, L.; Novak, P.; Vicente, R.; Hofmann, N. Angew. Chem., Int. Ed. 2009, 48,
26 3) Alkylation with alcohols geraniol Lee, D.-H.; Kwon, K.-H.; Yi, C. S. Science 2011, 333,
27 3) Alkylation with alcohols Lee, D.-H.; Kwon, K.-H.; Yi, C. S. Science 2011, 333,
28 3) Alkylation with alcohols 1 Lee, D.-H.; Kwon, K.-H.; Yi, C. S. Science 2011, 333,
29 3) Alkylation with alcohols C 5 H 8 Lee, D.-H.; Kwon, K.-H.; Yi, C. S. J. Am. Chem. Soc. 2012, 134,
30 3) Alkylation with alcohols 1 Lee, D.-H.; Kwon, K.-H.; Yi, C. S. J. Am. Chem. Soc. 2012, 134,
31 4) Acylation Kochi, T.; Urano, S.; Seki, H.; Mizushima, E.; Sato, M.; Kakiuchi, F. J. Am. Chem. Soc. 2009, 131,
32 4) Acylation Kochi, T.; Urano, S.; Seki, H.; Mizushima, E.; Sato, M.; Kakiuchi, F. J. Am. Chem. Soc. 2009, 131,
33 4) Acylation Zhao, X.; Dimitrijevic, E.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, Saidi, O.; Marafie, J.; Ledger, A. E. W.; Liu, P. M.; Mahon, M. F.; Kociok-Kohn, G.; Whittlesey, M. K.; Frost, C. G. J. Am. Chem. Soc. 2011, 133,
34 4) Acylation Saidi, O.; Marafie, J.; Ledger, A. E. W.; Liu, P. M.; Mahon, M. F.; Kociok-Kohn, G.; Whittlesey, M. K.; Frost, C. G. J. Am. Chem. Soc. 2011, 133,
35 4) Acylation Saidi, O.; Marafie, J.; Ledger, A. E. W.; Liu, P. M.; Mahon, M. F.; Kociok-Kohn, G.; Whittlesey, M. K.; Frost, C. G. J. Am. Chem. Soc. 2011, 133,
36 5) Alkenylation Yield 30-47% Weissman, H.; Song, X. P.; Milstein, D. J. Am. Chem. Soc. 2001, 123,
37 5) Alkenylation Yi, C. S.; Lee, D. W. Organometallics 2009, 28,
38 5) Alkenylation Kwon, K. H.; Lee, D. W.; Yi, C. S. Organometallics 2010, 29,
39 Question 2 5) Alkenylation Kwon, K. H.; Lee, D. W.; Yi, C. S. Organometallics 2010, 29,
40 5) Alkenylation Ueyama, T.; Mochida, S.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2011, 13, 706. Arockiam, P. B.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. H. Green Chem. 2011, 13,
41 5) Alkenylation Padala, K.; Jeganmohan, M. Org. Lett. 2011, 13,
42 5) Alkenylation Cheng, K.; Yao, B. B.; Zhao, J. L.; Zhang, Y. H. Org. Lett. 2008, 10,
43 5) Alkenylation Hashimoto, Y.; Hirano, K.; Satoh, T.; Kakiuchi, F.; Miura, M. Org. Lett. 2012, 14,
44 5) Alkenylation Ackermann, L.; Lygin, A. V.; Hofmann, N. Angew. Chem., Int. Ed. 2011, 50,
45 6) Others Thirunavukkarasu, V. S.; Hubrich, J.; Ackermann, L. Org. Lett. 2012, 14,
46 6) Others Thirunavukkarasu, V. S.; Ackermann, L. Org. Lett. 2013, /ol302956s 46
47 6) Others Yang, Y.; Lin, Y.; Rao, Y. Org. Lett. 2012, 14,
48 Summary Question 3 1. Frequently used Ru(II) catalysts: 2. Typical reactions 48
49 Summary Inexpesive Stable Multiple valents Many reaction types We have these Ru catalysts. Having an idea? Try it! Good luck!!! 49
50 Dec. 2,
51 Four different mechanisms for C H activation Question 1 Ru(0), Rh(I) Early transition metals Pd(II), Pd(IV), Ru(II), Rh(III) Pd(II), Ru(II) 51
52 Question 2 5) Alkenylation Ru(II) Ru(II) Ru(II) Ru(IV) Kwon, K. H.; Lee, D. W.; Yi, C. S. Organometallics 2010, 29,
53 Conclusion Question 3 1. Frequently used Ru(II/III) catalysts: 53
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