Chinese Journal of Organic Chemistry >
Application of Ligands in Cp*Rh(III)-Catalyzed C—H Bond Functionalization Reaction
Received date: 2022-11-29
Revised date: 2023-02-06
Online published: 2023-02-15
Supported by
National Natural Science Foundation of China(21671097); Fundamental Research Funds for the Central Universities
Cp*Rh(III) catalysts have shown excellent performance in the field of inert C—H bond functionalization because of their high activity and stability under mild conditions. However, limited by the number of Rh(III) coordination orbitals, the ligand studies in Cp*Rh(III) catalytic system are relatively few. Recently, our research group has been focusing on the external ligands promoted C—H bond functionalization with high activity and selectivity. In this review, the related works of Cp*Rh(III) catalyzed C—H bond functionalization are systematically summarized, including both symmetric and asymmetric C—H activation, the role of ligands in the Cp*Rh(III) catalytic system is discussed, and some reaction mechanisms are briefly described.
Key words: Cp*Rh(III); C—H bond functionalization; ligands
Yannian Pan , Xiao Qin , Chengkai Yuan , Yi Lu . Application of Ligands in Cp*Rh(III)-Catalyzed C—H Bond Functionalization Reaction[J]. Chinese Journal of Organic Chemistry, 2023 , 43(3) : 924 -948 . DOI: 10.6023/cjoc202211039
| [1] | (a) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068. |
| [1] | (b) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215. |
| [1] | (c) Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879. |
| [1] | (d) Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236. |
| [1] | (e) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107. |
| [1] | (f) Shin, K.; Kim, H.; Chang, S. Acc. Chem. Res. 2015, 48, 1040. |
| [1] | (g) Yang, Y.; Lan, J.; You, J. Chem. Rev. 2017, 117, 8787. |
| [1] | (h) Han, G.; Xu, H.; Hou, W. Chin. J. Org. Chem. 2022, 42, 391. (in Chinese) |
| [1] | (韩高旭, 许红涛, 侯卫, 有机化学, 2022, 42, 391.) |
| [2] | (a) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960. |
| [2] | (b) Su, L.; Yu, Z.; Ren, P.; Luo, Z.; Hou, W.; Xu, H. Org. Biomol. Chem. 2018, 16, 7236. |
| [2] | (c) Gandeepan, P.; Muller, T.; Zell, D.; Cera, G.; Warratz, S.; Ackermann, L. Chem. Rev. 2019, 119, 2192. |
| [2] | (d) Xu, H.; Gu, Y.; Zhang, S.; Xiong, H.; Ma, F.; Lu, F.; Ji, Q.; Liu, L.; Ma, P.; Hou, W.; Yang, G.; Lerner, R. A. Angew. Chem., Int. Ed. 2020, 59, 13273. |
| [2] | (e) Zhang, X.; Bai, R.; Xiong, H.; Xu, H.; Hou, W. Bioorg. Med. Chem. Lett. 2020, 30, 126916. |
| [2] | (f) Liu, S.; Zhuang, Z.; Qiao, J. X.; Yeung, K. S.; Su, S.; Cherney, E. C.; Ruan, Z.; Ewing, W. R.; Poss, M. A.; Yu, J. Q. J. Am. Chem. Soc. 2021, 143, 21657. |
| [2] | (g) Zhuang, Z.; Herron, A. N.; Liu, S.; Yu, J. Q. J. Am. Chem. Soc. 2021, 143, 687. |
| [2] | (h) Lee, M.; Heo, J.; Kim, D.; Chang, S. J. Am. Chem. Soc. 2022, 144, 3667. |
| [2] | (i) Li, Y.-H.; Ouyang, Y.; Chekshin, N.; Yu, J.-Q. ACS Catal. 2022, 12, 10581. |
| [3] | (a) Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212. |
| [3] | (b) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651. |
| [3] | (c) Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007. |
| [4] | Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362. |
| [5] | Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585. |
| [6] | (a) Zell, D.; Bursch, M.; Muller, V.; Grimme, S.; Ackermann, L. Angew. Chem., Int. Ed. 2017, 56, 10378. |
| [6] | (b) Satake, S.; Kurihara, T.; Nishikawa, K.; Mochizuki, T.; Hatano, M.; Ishihara, K.; Yoshino, T.; Matsunaga, S. Nat. Catal. 2018, 1, 585. |
| [7] | (a) Newton, C. G.; Wang, S. G.; Oliveira, C. C.; Cramer, N. Chem. Rev. 2017, 117, 8908. |
| [7] | (b) Shao, Q.; Wu, K.; Zhuang, Z.; Qian, S.; Yu, J. Q. Acc. Chem. Res. 2020, 53, 833. |
| [7] | (c) Zhang, J.; Lu, X.; Shen, C.; Xu, L.; Ding, L.; Zhong, G. Chem. Soc. Rev. 2021, 50, 3263. |
| [7] | (d) Zhang, Q.; Shi, B. F. Acc. Chem. Res. 2021, 54, 2750. |
| [8] | Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 4th ed., Hoboken, New Jersey, 2005, Chapter 5.4. |
| [9] | (a) Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118. |
| [9] | (b) Ackermann, L. Chem. Rev. 2011, 111, 1315. |
| [9] | (c) Davies, D. L.; Macgregor, S. A.; McMullin, C. L. Chem. Rev. 2017, 117, 8649. |
| [9] | (d) Alharis, R. A.; McMullin, C. L.; Davies, D. L.; Singh, K.; Macgregor, S. A. J. Am. Chem. Soc. 2019, 141, 8896. |
| [10] | Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350. |
| [11] | Shi, Z.; Schroder, N.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 8092. |
| [12] | Lu, Y.; Wang, H. W.; Spangler, J. E.; Chen, K.; Cui, P. P.; Zhao, Y.; Sun, W. Y.; Yu, J. Q. Chem. Sci. 2015, 6, 1923. |
| [13] | Shi, B. F.; Maugel, N.; Zhang, Y. H.; Yu, J. Q. Angew. Chem., Int. Ed. 2008, 47, 4882. |
| [14] | Liu, Y. Y.; Qu, Y. L.; Kang, Y. S.; Zhu, Y. L.; Sun, W. Y.; Lu, Y. Org. Lett. 2022, 24, 3118. |
| [15] | Umeda, N.; Tsurugi, H.; Satoh, T.; Miura, M. Angew. Chem.,Int. Ed. 2008, 47, 4019. |
| [16] | Zhang, P.; Chang, W.; Kang, Y. S.; Zhao, W.; Cui, P. P.; Liang, Y.; Sun, W. Y.; Lu, Y. Org. Lett. 2020, 22, 9462. |
| [17] | (a) Wang, P.; Li, G. C.; Jain, P.; Farmer, M. E.; He, J.; Shen, P. X.; Yu, J. Q. J. Am. Chem. Soc. 2016, 138, 14092. |
| [17] | (b) Zhu, R. Y.; Li, Z. Q.; Park, H. S.; Senanayake, C. H.; Yu, J. Q. J. Am. Chem. Soc. 2018, 140, 3564. |
| [18] | Shi, Y.; Fang, Y.; Zhao, X.; Zhu, C.; Wu, X.; Yang, X.; Luo, Y. Org. Lett. 2020, 22, 4903. |
| [19] | Wang, H. W.; Cui, P. P.; Lu, Y.; Sun, W. Y.; Yu, J. Q. J. Org. Chem. 2016, 81, 3416. |
| [20] | (a) Dai, H. X.; Yu, J. Q. J. Am. Chem. Soc. 2012, 134, 134. |
| [20] | (b) Thuy-Boun, P. S.; Villa, G.; Dang, D.; Richardson, P.; Su, S.; Yu, J. Q. J. Am. Chem. Soc. 2013, 135, 17508. |
| [20] | (c) Chan, K. S.; Wasa, M.; Chu, L.; Laforteza, B. N.; Miura, M.; Yu, J. Q. Nat. Chem. 2014, 6, 146. |
| [21] | Yuan, C. C.; Tu, G. L.; Zhao, Y. S. Org. Lett. 2017, 19, 356. |
| [22] | Kumar, R.; Parmar, D.; Gupta, S. S.; Chandra, D.; Dhiman, A. K.; Sharma, U. Chem.-Eur. J. 2020, 26, 4396. |
| [23] | Nunewar, S.; Kumar, S.; Talakola, S.; Nanduri, S.; Kanchupalli, V. Chem. Asian J. 2021, 16, 443. |
| [24] | Jeong, J.; Patel, P.; Hwang, H.; Chang, S. Org. Lett. 2014, 16, 4598. |
| [25] | Allu, S.; Ravi, M.; Swamy, K. C. Eur. J. Org. Chem. 2016, 2016, 5697. |
| [26] | Ravi, M.; Allu, S.; Swamy, K. C. J. Org. Chem. 2017, 82, 2355. |
| [27] | Das, D.; Poddar, P.; Maity, S.; Samanta, R. J. Org. Chem. 2017, 82, 3612. |
| [28] | Ghosh, B.; Samanta, R. Chem. Commun. 2019, 55, 6886. |
| [29] | Xue, Y.; Fan, Z. L.; Jiang, X. L.; Wu, K.; Wang, M. N.; Ding, C. Y.; Yao, Q. Z.; Zhang, A. Eur. J. Org. Chem. 2014, 2014, 7481. |
| [30] | Wang, H. W.; Lu, Y.; Zhang, B.; He, J.; Xu, H. J.; Kang, Y. S.; Sun, W. Y.; Yu, J. Q. Angew. Chem., Int. Ed. 2017, 56, 7449. |
| [31] | (a) Zhu, D.; Yang, G.; He, J.; Chu, L.; Chen, G.; Gong, W.; Chen, K.; Eastgate, M. D.; Yu, J. Q. Angew. Chem., Int. Ed. 2015, 54, 2497. |
| [31] | (b) He, J.; Shigenari, T.; Yu, J. Q. Angew. Chem., Int. Ed. 2015, 54, 6545. |
| [32] | Kang, Y. S.; Zhang, P.; Li, M. Y.; Chen, Y. K.; Xu, H. J.; Zhao, J.; Sun, W. Y.; Yu, J. Q.; Lu, Y. Angew. Chem., Int. Ed. 2019, 58, 9099. |
| [33] | Shi, H.; Dixon, D. J. Chem. Sci. 2019, 10, 3733. |
| [34] | Wakikawa, T.; Sekine, D.; Murata, Y.; Bunno, Y.; Kojima, M.; Nagashima, Y.; Tanaka, K.; Yoshino, T.; Matsunaga, S. Angew. Chem., Int. Ed. 2022, e202213659. |
| [35] | (a) Shibata, Y.; Tanaka, K. Angew. Chem., Int. Ed. 2011, 50, 10917. |
| [35] | (b) Piou, T.; Rovis, T. Acc. Chem. Res. 2018, 51, 170. |
| [35] | (c) Zhang, P.; Chang, W.; Jiao, H.; Kang, Y.; Zhao, W.; Cui, P.; Liang, Y.; Sun, W.-Y.; Lu, Y. Chin. Chem. Lett. 2021, 32, 1717. |
| [36] | Li, Y.; Zhang, X. S.; Zhu, Q. L.; Shi, Z. J. Org. Lett. 2012, 14, 4498. |
| [37] | Kong, L.; Zhou, X.; Xu, Y.; Li, X. Org. Lett. 2017, 19, 3644. |
| [38] | Saitou, T.; Jin, Y.; Isobe, K.; Suga, T.; Takaya, J.; Iwasawa, N. Chem. Asian J. 2020, 15, 1941. |
| [39] | (a) Tietze, L. F.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453. |
| [39] | (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442. |
| [39] | (c) Torborg, C.; Beller, M. Adv. Synth. Catal. 2009, 351, 3027. |
| [39] | (d) Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Chem. Rev. 2015, 115, 9587. |
| [40] | (a) Giri, R.; Shi, B. F.; Engle, K. M.; Maugel, N.; Yu, J. Q. Chem. Soc. Rev. 2009, 38, 3242. |
| [40] | (b) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704. |
| [40] | (c) Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 1926. |
| [40] | (d) Yang, L.; Huang, H. Catal. Sci. Technol. 2012, 2, 1099. |
| [40] | (e) Zheng, C.; You, S. L. RSC Adv. 2014, 4, 6173. |
| [40] | (f) Gao, D.-W.; Gu, Q.; Zheng, C.; You, S. L. Acc. Chem. Res. 2017, 50, 351. |
| [40] | (g) Saint-Denis, T. G.; Zhu, R. Y.; Chen, G.; Wu, Q. F.; Yu, J. Q. Science 2018, 359, 759. |
| [41] | Ye, B. H.; Cramer, N. Science 2012, 338, 504. |
| [42] | Shen, B.; Wan, B.; Li, X. Angew. Chem., Int. Ed. 2018, 57, 15534. |
| [43] | Cui, W. J.; Wu, Z. J.; Gu, Q.; You, S. L. J. Am. Chem. Soc. 2020, 142, 7379. |
| [44] | Yoshino, T.; Satake, S.; Matsunaga, S. Chem.-Eur. J. 2020, 26, 7346. |
| [45] | Yoshino, T.; Matsunaga, S. ACS Catal. 2021, 11, 6455. |
| [46] | Lin, L.; Fukagawa, S.; Sekine, D.; Tomita, E.; Yoshino, T.; Matsunaga, S. Angew. Chem., Int. Ed. 2018, 57, 12048. |
| [47] | Fukagawa, S.; Kojima, M.; Yoshino, T.; Matsunaga, S. Angew. Chem., Int. Ed. 2019, 58, 18154. |
| [48] | Fukagawa, S.; Kato, Y.; Tanaka, R.; Kojima, M.; Yoshino, T.; Matsunaga, S. Angew. Chem., Int. Ed. 2019, 58, 1153. |
| [49] | Huang, L. T.; Fukagawa, S.; Kojima, M.; Yoshino, T.; Matsunaga, S. Org. Lett. 2020, 22, 8256. |
| [50] | Kato, Y.; Lin, L.; Kojima, M.; Yoshino, T.; Matsunaga, S. ACS Catal. 2021, 11, 4271. |
| [51] | Pham, M. V.; Cramer, N. Chem.-Eur. J. 2016, 22, 2270. |
| [52] | Sun, Y.; Cramer, N. Angew. Chem., Int. Ed. 2018, 57, 15539. |
| [53] | Wang, Q.; Zhang, W. W.; Song, H.; Wang, J.; Zheng, C.; Gu, Q.; You, S. L. J. Am. Chem. Soc. 2020, 142, 15678. |
| [54] | Wang, Q.; Zhang, W. W.; Zheng, C.; Gu, Q.; You, S. L. J. Am. Chem. Soc. 2021, 143, 114. |
/
| 〈 |
|
〉 |