First Row TM Catalyzed C-H Activation. Zhi Ren 2014/9/10
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1 First Row TM Catalyzed C-H Activation Zhi Ren 2014/9/10
2 Outline 1. Introduction 2. Sc catalyzed C-H activation 3. Ti catalyzed C-H activation 4. V catalyzed C-H oxidation/fluorination 5. Mn catalyzed C-H activation 6. Fe catalyzed C-H activation 7. Ni catalyzed C-H activation 8. Summary
3 Introduction First row metal catalyzed C-H activation is much less compare to the second row. Most of them are cheaper than the second row. V, Mn and Cr are well known to oxidation C-H bonds, but most through radical process, which metal is not attached to
4 Introduction Price comparation: Which metal is the most expensive and which is the least expensive one? Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn
5 Introduction Price comparation: Sc $ /mol Co $ /mol V $210.43/mol Cr $161.18/mol Mn $40.51/mol Ti $4.63/mol Ni $1.12/mol Cu $0.45/mol Zn $0.15/mol Fe $0.0054/mol
6 Sc catalyzed C-H activation Sc works as LA in most reactions it catalyzed. The directed catalytic C-H activation works are all from Zhaomin Hou s group. Sc complex can activate methane. These works are from Don Tilley s group.
7 Sc catalyzed C-H activation
8 Sc catalyzed C-H activation
9 Sc catalyzed C-H activation
10 Sc catalyzed C-H activation
11 Sc catalyzed C-H activation
12 Sc catalyzed C-H activation
13 Sc catalyzed C-H activation Don Tilley s group 50 turnovers! After 4 days: 85% 42% 15% s-bond metathesis Angew. Chem. Int. Ed. 2003, 42, No. 7, 803
14 Sc catalyzed C-H activation Don Tilley s group
15 Ti catalyzed C-H activation Ti works as LA in most reactions it catalyzed. Ti is also know for polymerization of alkenes. The hydroaminoalkylation reactions presented are all from Sven Doye s group. The most common hydroaminoalkylation reactions are catalyzed by Ta.
16 Ti catalyzed C-H activation
17 Ti catalyzed C-H activation
18 Ti catalyzed C-H activation
19 Ti catalyzed C-H activation
20 Ti catalyzed C-H activation
21 Ti catalyzed C-H activation
22 Ti catalyzed C-H activation
23 Ti catalyzed C-H activation
24 V catalyzed C-H activation V is widely use in oxidation of C-H bonds. Nature Chemistry, 2010, 2, 478. V catalyzed C-H activation is hard to found. The two C-H functionalization reactions are from Chuo Chen s group.
25 V catalyzed C-H oxidation
26 V catalyzed C-H Florination
27 Mn catalyzed C-H activation Mn is widely use in oxidation of C-H bonds. Mn catalyzed C-H activation is not well developed. Only a few examples. The work was discovered by Prof. Takai, and followed by Congyang Wang.
28 Mn catalyzed C-H Activation Kazuhiko Takai and Yoichiro Kuninobu s work
29 Mn catalyzed C-H Activation Wang s work
30 Mn catalyzed C-H Activation
31 Mn catalyzed C-H Activation
32 Mn catalyzed C-H Activation
33 Fe catalyzed C-H activation There are too many Fe catalyzed C-H activation reactions. Zhangjie Shi, Chemical Reviews 2010, 111, Eiichi Nakamura, J. Org. Chem. 2010, 75, The following works are all from Prof. Nakamura s group.
34 Fe catalyzed C-H Activation % yield % yield mono di
35 Fe catalyzed C-H Activation
36 Fe catalyzed C-H Activation
37 Org. Lett., 2013, 15, 714 Fe catalyzed C-H Activation
38 Fe catalyzed C-H Activation
39 Fe catalyzed C-H Activation
40 Fe catalyzed C-H Activation
41 Fe catalyzed C-H Activation
42 Co catalyzed C-H activation Huang presented the Co catalyzed C-H activation during his talk. Yoshikai, N., Acc. Chem. Res. 2014, 47, This Friday, I will present two Co catalyzed C-H activation from Prof. Olafs Daugulis.
43 Ni catalyzed C-H activation Ni catalyzed cross coupling reaction was well established. For recent Nickel catalysis: Nature 2014, 509, 299. The following works are all from Prof. Chatani s group.
44 Ni catalyzed C-H Activation
45 Ni catalyzed C-H Activation
46 Ni catalyzed C-H Activation
47 Cu catalyzed C-H activation Cu catalyzed C-H activation reactions are well established. Acc. Chem. Res., 2012, 45 (6), pp Chem. Rev., 2013, 113 (8), pp
48 Summary 1. Sc and Ti are very lewis acidic, and also oxygenphilic. The ligand development is very important in these type reaction. 2. For V, Cr, and Mn, the catalyzed C-H activation reactions are underdeveloped. Use the low-valent species are important. 3. For Fe, Co, Ni and Cu system, it is now a rapid growing area.
49 Thanks!
50 Questions!
51 Questions!
52 Questions!
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