Citation: Liu Lu, Zhang Junliang. Development of Transition-Metal-Catalyzed C(sp²)-H Functionalization of Arenes with Diazo Compounds[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1117-1126. doi: 10.6023/cjoc201702020 shu

Development of Transition-Metal-Catalyzed C(sp²)-H Functionalization of Arenes with Diazo Compounds

Liu Lu ^*,, ,
Zhang Junliang ^*,,

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241

Corresponding author: Liu Lu, lliu@chem.ecnu.edu.cn Zhang Junliang,
Received Date: 16 February 2017
Revised Date: 10 March 2017

Fund Project: the National Natural Science Foundation of China Nos. 21372084the National Natural Science Foundation of China 21425205the National Natural Science Foundation of China 21572065the National Basic Research Program of China No. 2015CB856600the National Basic Research Program of China 973 Programthe Shanghai Pujiang Program No. 14PJ1403100

Figures(18)

C-H bond functionalization has been one of the most important subject in chemistry. How to control the site selectivity of C-H bond is the key issue and remain challenge. Transition-metal-catalyzed organic tranformation of diazo compounds, such as X-H (X=O, N, S, etc.) insertion, cyclopropanation, cross-coupling reactions and C(sp³)-H functionalization, have been well established, whereas the C(sp²)-H functionalization using diazo compounds is less developed. This review will summarize the progress in transition-metal-catalyzed C(sp²)-H functionalization of arenes with diazo compounds. To realize the site selectivity, two strategies are utilized. One is directed C-H activation, which gives the ortho-selective C-H functionalization products. The other is undirected approach, which normally exhibits para-selectivity. In order to understand these reactions, the mechanisms for selected examples are also provided.
- tansition-metal-catalysis,
- diazo compound,
- arene,
- C-H bond functionalization,
- site selective
1. [1]
2. [2]
  (a) Liu, L.; Zhang, J. Chem. Soc. Rev. 2016, 45, 506.
  (b) Fructos, M. R.; Díaz-Requejo, M. M.; Pérez, P. J. Chem. Commun. 2016, 52, 7326.
  (c) Wei, F.; Song, C.; Ma, Y.; Zhou, L.; Tung, C.-H.; Xu, Z. Sci. Bull. 2015, 60, 1479.
  (d) Ford, A.; Miel, H.; Ring, A.; Slattery, C. N.; Maguire, A. R.; Mckervey, M. A. Chem. Rev. 2015, 115, 9981.
  (e) Davies, H. M. L.; Lian, Y.-J. Acc. Chem. Res. 2012, 45, 923.
  (f) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577.
  (g) Maas, G. Chem. Soc. Rev. 2004, 33, 183.
  (h) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
  (i) Doyle, M. P.; McKervey, M. A. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998.
  (j) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
  (k) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704.
3. [3]
  (a) Davies, H. M. L.; Manning, J.-R. Nature 2008, 451, 417.
  (b) Díaz-Requejo, M. M.; Pérez, P. J. Chem. Rev. 2008, 108, 3379.
  (c) Liu, Z.; Wang, J. J. Org. Chem. 2013, 78, 10024.
4. [4]
  Silberrad, O.; Roy, C. S. J. Chem. Soc. 1906, 179.
5. [5]
  (a) Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857.
  (b) Liao, K.; Negretti, S.; Musaev, D. G.; Bacsa, J.; Davies, H. M. L. Nature 2016, 533, 230.
6. [6]
  http://ibond.nankai.edu.cn.
7. [7]
  (a) Cheng, C.; Hartwig, J. F. Chem. Rev. 2015, 115, 8946.
  (b) Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007.
  (c) Ye, B.; Cramer, N. Acc. Chem. Res. 2015, 48, 1308.
  (d) Shin, K.; Kim, H.; Chang, S. Acc. Chem. Res. 2015, 48, 1040.
  (e) Daugulis, O.; Roane, J.; Tran, L. D. Acc. Chem. Res. 2015, 48, 1053.
  (f) Segawa, Y.; Maekawa, T.; Itami, K. Angew. Chem., Int. Ed. 2015, 54, 66.
  (g) Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74.
  (h) Gao, K.; Yoshikai, N. Acc. Chem. Res. 2014, 47, 1208.
  (i) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726.
  (j) Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369.
  (k) Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879.
  (l) Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588.
  (m) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
  (n) Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2011, 45, 788;
8. [8]
  Chan, W.-W.; Lo, S.-F.; Zhou, Z.; Yu, W.-Y. J. Am. Chem. Soc. 2012, 134, 13565. doi: 10.1021/ja305771y
9. [9]
  (a) Hyster, T. K.; Ruhl, K. E.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 5364.
  (b) Shi, Z.; Koester, D. C.; Boultadakis-Arapinis, M.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 12204.
  (c) Hu, F.; Xia, Y.; Ye, F.; Liu, Z.; Ma, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 1364.
  (d) Yu, S.; Liu, S.; Lan, Y.; Wan, B.; Li, X. J. Am. Chem. Soc. 2015, 137, 1623.
  (e) Yu, X.; Yu, S.; Xiao, J.; Wan, B.; Li, X. J. Org. Chem. 2013, 78, 5444.
  (f) Cheng, Y.; Bolm, C. Angew. Chem., Int. Ed. 2015, 54, 12349.
  (g) Cui, S.; Zhang, Y.; Wang, D.; Wu, Q. Chem. Sci. 2013, 4, 3912.
  (h) Dateer, R. B.; Chang, S. Org. Lett. 2016, 18, 68.
  (i) Liang, Y.; Yu, K.; Li, B.; Xu, S.; Song, H.; Wang, B. Chem. Commun. 2014, 50, 6130.
  (j) Zhou, T.; Li, B.; Wang, B. Chem. Commun. 2016, 52, 14117.
  (k) Zhou, J.; Shi, J.; Liu, X.; Jia, J.; Song, H.; Xu, H. E.; Yi, W. Chem. Commun. 2015, 51, 5868.
  (l) Son, J.-Y.; Kim, S.; Jeon, W. H.; Lee, P. H. Org. Lett. 2015, 17, 2518.
  (m) Bai, P.; Huang, X.-F.; Xu, G.-D.; Huang, Z.-Z. Org. Lett. 2016, 18, 3058.
  (n) Song, C.; Yang, C.; Zhang, F.; Wang, J.; Zhu, J. Org. Lett. 2016, 18, 4510.
10. [10]
  Ye, B.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 7896. doi: 10.1002/anie.201404895
11. [11]
  (a) Phatake, R. S.; Patel, P.; Ramana, C. V. Org. Lett. 2016, 18, 292.
  (b) Phatake, R. S.; Patel, P.; Ramana, C. V. Org. Lett. 2016, 18, 2828.
  (c) Patel, P.; Borah, G. Chem. Commun. 2017, 53, 443.
12. [12]
  (a) Zhao, D.; Kim, J. H.; Stegemann, L.; Strassert, C. A.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 4508.
  (b) Kim, J. H.; Greßies, S.; Glorius, F. Angew. Chem., Int. Ed. 2016, 55, 5577.
13. [13]
  Li, J.; Tang, M.; Zang, L.; Zhang, X.; Zhang, Z.; Ackermann, L. Org. Lett. 2016, 18, 2742. doi: 10.1021/acs.orglett.6b01199
14. [14]
  Yu, Z.; Li, Y.; Shi, J.; Ma, B.; Liu, L.; Zhang, J. Angew. Chem., Int. Ed. 2016, 55, 14807. doi: 10.1002/anie.201608937
15. [15]
  Hartwig, J. F.; Larsen, M. A. ACS Cent. Sci. 2016, 2, 281. doi: 10.1021/acscentsci.6b00032
16. [16]
  Yates, P. J. Am. Chem. Soc. 1952, 74, 5376. doi: 10.1021/ja01141a047
17. [17]
  (a) Gillingham, D.; Fei, N. Chem. Soc. Rev. 2013, 42, 4918.
  (b) Guo, X.; Hu, W. Acc. Chem. Res. 2013, 46, 2427.
  (c) Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2012, 45, 1365.
  (d) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811.
18. [18]
  Yu, Z.; Ma, B.; Chen, M.; Wu, H.-H.; Liu, L.; Zhang, J. J. Am. Chem. Soc. 2014, 136, 6904. doi: 10.1021/ja503163k
19. [19]
  Fan, H.; Zhang, Z.; Li, X.; Zhao, J.; Gao, J.; Zhu, S. Tetrahedron 2013, 69, 1978. doi: 10.1016/j.tet.2012.12.077
20. [20]
  Tayama, E.; Yanaki, T.; Iwamoto, H.; Hasegawa, E. Eur. J. Org. Chem. 2010, 6719.
21. [21]
  Tayama, E.; Ishikawa, M.; Iwamoto, H.; Hasegawa, E. Tetrahedron Lett. 2012, 53, 5159. doi: 10.1016/j.tetlet.2012.07.070
22. [22]
  Xi, Y.; Su, Y.; Yu, Z.; Dong, B.; McClain, E. J.; Lan, Y.; Shi, X. Angew. Chem., Int. Ed. 2014, 53, 9817. doi: 10.1002/anie.201404946
23. [23]
  Liu, Y.; Yu, Z.; Zhang, J. Z.; Liu, L, Xia, F.; Zhang, J. Chem. Sci. 2016, 7, 1988. doi: 10.1039/C5SC04319K
24. [24]
  Liu, Y.; Yu, Z.; Luo, Z.; Zhang, J. Z.; Liu, L, Xia, F. J. Phys. Chem. A 2016, 120, 1925. doi: 10.1021/acs.jpca.6b00636
25. [25]
  Yang, J.-M.; Cai, Y.; Zhu, S.-F.; Zhou, Q.-L. Org. Biomol. Chem. 2016, 14, 5516. doi: 10.1039/C5OB02418H
26. [26]
  Magar, K. B. S.; Edison, T. N. J. I.; Lee, Y. R. Org. Biomol. Chem. 2016, 14, 7313. doi: 10.1039/C6OB01315E
27. [27]
  Yu, Z.; Qiu, H.; Liu, L.; Zhang, J. Chem. Commun. 2016, 52, 2257. doi: 10.1039/C5CC08880A
28. [28]
  Jia, S.; Lei, Y.; Song, L.; Reddy, A. G. K.; Xing, D.; Hu, W. Adv. Synth. Catal. 2017, 359, 58. doi: 10.1002/adsc.v359.1
29. [29]
  Ma, B.; Wu, Z.; Huang, B.; Liu, L.; Zhang, J. Chem. Commun. 2016, 52, 9351. doi: 10.1039/C6CC04034A
30. [30]
  Jia, S.; Xing, D.; Zhang, D.; Hu, W. Angew. Chem., Int. Ed. 2014, 53, 13098. doi: 10.1002/anie.201406492
31. [31]
  Xu, B.; Li, M.-L.; Zuo, X.-D.; Zhu, S.-F.; Zhou, Q.-L. J. Am. Chem. Soc. 2015, 137, 8700. doi: 10.1021/jacs.5b05086
32. [32]
  Cao, Z.; Zhao, Y.; Zhou, J. Chem. Commun. 2016, 52, 2537. doi: 10.1039/C5CC10096H
33. [33]
  Rosenfeld, M. J.; Shankar, B. K.; Shechter, H. J. Org. Chem. 1988, 53, 2699. doi: 10.1021/jo00247a007
34. [34]
  Mbuvi, H. M.; Woo, L. K. Organometallics 2008, 27, 637. doi: 10.1021/om7007502
35. [35]
  Best, D.; Burns, D. J.; Lam, H. W. Angew. Chem., Int. Ed. 2015, 54, 7410. doi: 10.1002/anie.v54.25
36. [36]
  Best, D.; Jean, M.; van de Weghe, P. J. Org. Chem. 2016, 81, 7760. doi: 10.1021/acs.joc.6b01426
37. [37]
  Fructos, M. R.; Belderrain, T. R.; de Frémont, P.; Scott, N. M.; Nolan, S. P.; Díaz-Requejo, M. M.; Pérez, P. J. Angew. Chem., Int. Ed. 2005, 44, 5284. doi: 10.1002/(ISSN)1521-3773
38. [38]
  Rivilla, I.; Gõmez-Emeterio, B. P.; Fructos, M. R.; Díaz-Requejo, M. M.; Perez, P. J. Organometallics 2011, 30, 2855. doi: 10.1021/om200206m
39. [39]
  Conde, A.; Sabenya, G.; Rodríguez, M.; Postils, V.; Luis, J. S.; Díaz-Requejo, M. M.; Costas, M.; Pérez, P. J. Angew. Chem., Int. Ed. 2016, 55, 6530. doi: 10.1002/anie.201601750
40. [40]
  Ma, B.; Chu, Z.; Huang, B.; Liu, Z.; Liu, L.; Zhang, J. Angew. Chem., Int. Ed. 2017, 56, 2749. doi: 10.1002/anie.v56.10
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Development of Transition-Metal-Catalyzed C(sp2)-H Functionalization of Arenes with Diazo Compounds

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Development of Transition-Metal-Catalyzed C(sp²)-H Functionalization of Arenes with Diazo Compounds