Top 10 Challenges for Catalysis
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1 Top 10 Challenges for Catalysis 1
2 difficulty Ammonia Anti-Markovnikov Hydroamination Olefin Not achieved Anti-Markovnikov Hydroamination Olefin (Aromatic Aliphatic) Hydroamination Olefin Anti-Markovnikov Intermolecular Hydroamination of Olefins and Relative Mechanism Studies Reporter: Fanyang Mo Supervisor: Prof. Dr. Guangbin Dong UT Ausitn 2
3 Content Reactions 1. Anti-Markovnikov hydroamination of olefin a. Alkali-metal-catalyzed/mediated (Li, Na) b. Transition-metal-catalyzed (Rh, Ru, Cu ) c. Non-catalyzed Mechanism and Insights 2. Migratory Insertion of Olefins into Metal Nitrogen Bonds 3. Activation of N-H bond 3
4 1. Anti-Markovnikov hydroamination of olefin a. Alkali-metal-catalyzed/mediated (Li, Na) Kumar, K.; Michalik, D.; Garcia Castro, I.; Tillack, A.; Zapf, A.; Arlt, M.; Heinrich, T.; Böttcher, H.; Beller, M. Chemistry A European Journal 2004, 10,
5 1. Anti-Markovnikov hydroamination of olefin a. Alkali-metal-catalyzed/mediated (Li, Na) Khedkar, V.; Tillack, A.; Benisch, C.; Melder, J.-P.; Beller, M. J. Mol. Catal. A: Chem. 2005, 241,
6 1. Anti-Markovnikov hydroamination of olefin a. Alkali-metal-catalyzed/mediated (Li, Na) Khedkar, V.; Tillack, A.; Benisch, C.; Melder, J.-P.; Beller, M. J. Mol. Catal. A: Chem. 2005, 241,
7 1. Anti-Markovnikov hydroamination of olefin a. Alkali-metal-catalyzed/mediated (Li, Na) Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, P
8 1. Anti-Markovnikov hydroamination of olefin (aromatic) b. Transition-metal-catalyzed Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Müller, T. E. Eur. J. Inorg. Chem. 1999, 1999,
9 1. Anti-Markovnikov hydroamination of olefin b. Transition-metal-catalyzed Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Müller, T. E. Eur. J. Inorg. Chem. 1999, 1999,
10 Two equiv Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Müller, T. E. Eur. J. Inorg. Chem. 1999, 1999,
11 1. Anti-Markovnikov hydroamination of olefin b. Transition-metal-catalyzed Utsunomiya, M.; Kuwano, R.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125,
12 Amine : olefin = 1:4 Substrates limitation: Primary aliphatic amine and aromatic amine did not react. Utsunomiya, M.; Kuwano, R.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125,
13 Concentration of olefin affected the amine:enamine ratio very much. Utsunomiya, M.; Kuwano, R.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125,
14 1. Anti-Markovnikov hydroamination of olefin b. Transition-metal-catalyzed Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126,
15 Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126,
16 Takaya, J.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127,
17 Takaya, J.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127,
18 1. Anti-Markovnikov hydroamination of olefin b. Transition-metal-catalyzed Bronner, S. M.; Grubbs, R. H. Chem. Sci. 2014, 5,
19 Bronner, S. M.; Grubbs, R. H. Chem. Sci. 2014, 5,
20 Substrate limitation: aromatic amines Bronner, S. M.; Grubbs, R. H. Chem. Sci. 2014, 5,
21 1. Anti-Markovnikov hydroamination of olefin b. Transition-metal-catalyzed Zhu, S.; Niljianskul, N.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135,
22 1. Anti-Markovnikov hydroamination of olefin b. Transition-metal-catalyzed DEMS: di-etmesih Zhu, S.; Niljianskul, N.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135,
23 1. Anti-Markovnikov hydroamination of olefin b. Transition-metal-catalyzed Zhu, S.; Niljianskul, N.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135,
24 1. Anti-Markovnikov hydroamination of olefin c. Non-catalyzed Question 1: Strom, A. E.; Hartwig, J. F. J. Org. Chem. 2013, 78,
25 Content Reactions 1. Anti-Markovnikov hydroamination of olefin a. Alkali-metal-catalyzed/mediated (Li, Na) b. Transition-metal-catalyzed (Rh, Ru, Cu ) c. Non-catalyzed Mechanism and Insights 2. Migratory Insertion of Olefins into Metal Nitrogen Bonds 3. Activation of N-H bond 25
26 2. Migratory Insertion of Olefins into Metal Nitrogen Bonds a. Pd-N bond Brice, J. L.; Harang, J. E.; Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2005, 127,
27 2. Migratory Insertion of Olefins into Metal Nitrogen Bonds a. Pd-N bond Question 3: Neukom, J. D.; Perch, N. S.; Wolfe, J. P. J. Am. Chem. Soc. 2010, 132,
28 2. Migratory Insertion of Olefins into Metal Nitrogen Bonds a. Pd-N bond Hanley, P. S.; Marković, D.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132,
29 2. Migratory Insertion of Olefins into Metal Nitrogen Bonds a. Pd-N bond Hanley, P. S.; Marković, D.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132,
30 2. Migratory Insertion of Olefins into Metal Nitrogen Bonds a. Pd-N bond Question 2: Hanley, P. S.; Marković, D.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132,
31 2. Migratory Insertion of Olefins into Metal Nitrogen Bonds b. Pt-N bond Cowan, R. L.; Trogler, W. C. Organometallics 1987, 6,
32 2. Migratory Insertion of Olefins into Metal Nitrogen Bonds c. Ir-N bond ZnCl 2 Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110,
33 2. Migratory Insertion of Olefins into Metal Nitrogen Bonds d. Rh-N bond Zhao, P.; Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127,
34 3. Activation of N-H bond X-ray Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. Inorg. Chem. 1987, 26,
35 3. Activation of N-H bond Khaskin, E.; Iron, M. A.; Shimon, L. J. W.; Zhang, J.; Milstein, D. J. Am. Chem. Soc. 2010, 132, Feller, M.; Diskin-Posner, Y.; Shimon, L. J. W.; Ben-Ari, E.; Milstein, D. Organometallics 2012, 31,
36 3. Activation of N-H bond Kanzelberger, M.; Zhang, X.; Emge, T. J.; Goldman, A. S.; Zhao, J.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125,
37 3. Activation of N-H bond Zhao, J.; Goldman, A. S.; Hartwig, J. F. Science 2005, 307,
38 3. Activation of N-H bond Zhao, J.; Goldman, A. S.; Hartwig, J. F. Science 2005, 307,
39 3. Activation of N-H bond Zhou, J.; Hartwig, J. F. Angew. Chem. Int. Ed. 2008, 47,
40 3. Activation of N-H bond Sykes, A. C.; White, P.; Brookhart, M. Organometallics 2006, 25,
41 3. Activation of N-H bond Sykes, A. C.; White, P.; Brookhart, M. Organometallics 2006, 25,
42 3. Activation of N-H bond Fafard, C. M.; Adhikari, D.; Foxman, B. M.; Mindiola, D. J.; Ozerov, O. V. J. Am. Chem. Soc. 2007, 129,
43 3. Activation of N-H bond Fafard, C. M.; Adhikari, D.; Foxman, B. M.; Mindiola, D. J.; Ozerov, O. V. J. Am. Chem. Soc. 2007, 129,
44 4. Conclusion a. NH 3 + Olefin Catalytic utilization of ammonia in olefin hydroamination and in coupling with arenes were listed among the top ten challenges for catalysis over a decade ago, and these remain unsolved today. b. NHRR + Olefin Markovnikov + aromatic olefin Markovnikov + aliphatic olefin Anit-Markovnikov + aromatic olefin Anit-Markovnikov + aliphatic olefin c. Any chance? Activation of olefin Activation of amine Markovnikov 44
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