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
1. [1]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
2. [2]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
3. [3]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
4. [4]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
5. [5]
  Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
6. [6]
  Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
7. [7]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
8. [8]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
9. [9]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
10. [10]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
11. [11]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
12. [12]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
13. [13]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-0. doi: 10.3866/PKU.WHXB202407005
14. [14]
  Xinwan Zhao , Yue Cao , Minjun Lei , Zhiliang Jin , Tsubaki Noritatsu . Constructing S-scheme heterojunctions by integrating covalent organic frameworks with transition metal sulfides for efficient noble-metal-free photocatalytic hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(12): 100152-0. doi: 10.1016/j.actphy.2025.100152
15. [15]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
16. [16]
  Feifei Yang , Wei Zhou , Chaoran Yang , Tianyu Zhang , Yanqiang Huang . Enhanced Methanol Selectivity in CO₂ Hydrogenation by Decoration of K on MoS₂ Catalyst. Acta Physico-Chimica Sinica, 2024, 40(7): 2308017-0. doi: 10.3866/PKU.WHXB202308017
17. [17]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
18. [18]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
19. [19]
  Xinyu Xu , Jiale Lu , Bo Su , Jiayi Chen , Xiong Chen , Sibo Wang . Steering charge dynamics and surface reactivity for photocatalytic selective methane oxidation to ethane over Au/Ti-CeO₂. Acta Physico-Chimica Sinica, 2025, 41(11): 100153-0. doi: 10.1016/j.actphy.2025.100153
20. [20]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385

Get Citation

PDF

XML

Metrics

PDF Downloads(19)
Abstract views(4646)
HTML views(2084)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

Metrics

通讯作者: 陈斌, bchen63@163.com

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