SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 2: 391 - 423

DOI: https://doi.org/10.6023/cjoc202108012

REVIEWS

Rhodium(III) Catalyzed C(sp3)—H Functionalization

  • Gaoxu Han ,
  • Hongtao Xu ,
  • Wei Hou
Expand
  • a Institute of Drug Development & Chemical Biology, College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014
    b Shanghai Institute for Advanced Immunochemical Studies, ShanghaiTech University, Shanghai 201210
* Corresponding authors. E-mail: ;

Received date: 2021-08-10

  Revised date: 2021-09-22

  Online published: 2022-02-24

Supported by

National Natural Science Foundation of China(21907085)

Fold

Abstract

The outer electron of trivalent rhodium is d6, which is very electron deficient. Therefore, the C—Rh(III) bond formed by Rh(III) catalyzed C—H activation is of big polarity and can react with a variety of terminal reagents containing polar bonds, thus forming a good cross complementarity with palladium and other metals. In recent years, significant progress has been made in the Rh(III) catalyzed C(sp2)—H bond functionalization. And many of the reported methods have been applied in heterocyclic skeleton construction and drug modification more and more frequently. Although the activation mechanism of inert C(sp3)—H bond is similar to that of C(sp2)—H bond, the bond energy of C(sp3)—H bond is more stronger, and there is no π electron easily to interact with the metal center, so the exploration and research in this field still face arduous challenges. The research progress in Rh(III) catalyzed C(sp3)—H functionalization is systematically summarized and the reported work is classified into different reaction types.

Key words： rhodium(III); C(sp3)—H functionalization; alkylation; arylation; carbonylation; alkenylation; amination; cyclization

Cite this article

Gaoxu Han , Hongtao Xu , Wei Hou . Rhodium(III) Catalyzed C(sp3)—H Functionalization[J]. Chinese Journal of Organic Chemistry, 2022 , 42(2) : 391 -423 . DOI: 10.6023/cjoc202108012

References

[1]
Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068.
[2]
Yang, Y.; Lan, J.; You, J. Chem. Rev. 2017, 117, 8787.
[3]
Dyker, G. J. Am. Chem. Soc. 2006, 128, 5982.
[4]
Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., nt. Ed. 2012, 51, 8960.
[5]
Gandeepan, P.; Muller, T.; Zell, D.; Cera, G.; Warratz, S.; Ackermann, L. Chem. Rev. 2019, 119, 2192.
[6]
Su, L.; Yu, Z.; Ren, P.; Luo, Z.; Hou, W.; Xu, H. Org. Biomol. Chem. 2018, 16, 7236.
[7]
Hou, W.; Xiong, H.; Bai, R. S.; Xiao, Z. Z.; Su, L.; Ruan, B. H.; Xu, H. Tetrahedron 2019, 75, 4005.
[8]
Su, L.; Hou, W. Chin. J. Org. Chem. 2019, 39, 363. (in Chinese)
[8]
( 苏琳, 侯卫, 有机化学, 2019, 39, 363.)
[9]
Xiong, H.; Gu, Y.; Zhang, S.; Lu, F.; Ji, Q.; Liu, L.; Ma, P.; Yang, G.; Hou, W.; Xu, H. Chem. Commun. 2020, 56, 4692.
[10]
Zhang, X.; Bai, R.; Xiong, H.; Xu, H.; Hou, W. Bioorg. Med. Chem. Lett. 2020, 30, 126916.
[11]
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.
[12]
Shan, B.; Miao, Q.; Wang, R.; Jia, G. H.; Zhao, H. Q. Catal. Commun. 2019, 128, 105701.
[13]
Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654.
[14]
Godula, K.; Sames, D. Science 2006, 312, 67.
[15]
Chen, H. Y.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
[16]
Chen, Z.; Rong, M. Y.; Nie, J.; Zhu, X. F.; Shi, B. F.; Ma, J. A. Chem. Soc. Rev. 2019, 48, 4921.
[17]
Rej, S.; Chatani, N. Angew. Chem., Int. Ed. 2019, 58, 8304.
[18]
Li, H.; Li, B. J.; Shi, Z. J. Catal. Sci. Technol. 2011, 1, 191.
[19]
Dai, Y. Q.; Li, X. W.; Liu, B. X. Chin. J. Org. Chem. 2021, 41, 4476. (in Chinese)
[19]
( 戴雨倩, 李兴伟, 刘丙贤, 有机化学, 2021, 41, 4476.)
[20]
Dong, Z. Z.; Li, P. F.; Li, X. W.; Liu, B. X. Chin. J. Chem. 2021, 39, 2489.
[21]
Wang, Z. T.; Zheng, Z. A.; Li, P. J.; Zhou, C. N.; Cai, S. J.; Xiao, B.; Wang, L. Chin. J. Chem. 2021, 39, 2823.
[22]
Liu, B. X.; Yang, L. Y.; Li, P. F.; Wang, F.; Li, X. W. Org. Chem. Front. 2021, 8, 1085.
[23]
Song, G.; Li, X. W. Acc. Chem. Res. 2015, 48, 1007.
[24]
Song, G.; Wang, F.; Li, X. W. Chem. Soc. Rev. 2012, 41, 3651.
[25]
Kuhl, N.; Schröder, N.; Glorius, F. Adv. Synth. Catal. 2014, 356, 1443.
[26]
Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585.
[27]
Liu, B. X.; Zhou, T.; Li, B.; Xu, S. S.; Song, H. B.; Wang, B. Q. Angew. Chem., Int. Ed. 2014, 53, 4191.
[28]
Wang, N. C.; Li, R. H.; Li, L. B.; Xu, S. S.; Song, H. B.; Wang, B. Q. J. Org. Chem. 2014, 79, 5379.
[29]
Mishra, A. A.; Subhedar, D.; Bhanage, B. M. Chem. Rec. 2019, 19, 1829.
[30]
Yang, X. L.; Shan, G.; Wang, L. G.; Rao, Y. Tetrahedron Lett. 2016, 57, 819.
[31]
Yoshino, T.; Matsunaga, S. Adv. Organomet. Chem. 2017, 68, 197.
[32]
Yoshino, T.; Matsunaga, S. Asian J. Org. Chem. 2018, 7, 1193.
[33]
Tsukano, C. Chem. Pharm. Bull. 2017, 65, 409.
[34]
He, C.; Whitehurst, W. G.; Gaunt, M. J. Chem 2019, 5, 1.
[35]
Das, A.; Maji, B. Asian J. Chem. 2021, 16, 397.
[36]
Zhao, K.; Yang, L.; Liu, J. H.; Xia, C. G. Chin. J. Org. Chem. 2018, 38, 2833. (in Chinese)
[36]
( 赵康, 杨磊, 刘建华, 夏春谷, 有机化学, 2018, 38, 2833.)
[37]
Zhan, B. B.; Jiang, M. X.; Shi, B. F. Chem. Commun. 2020, 56, 13950.
[38]
Alexander, U.; Manuel, V. G. Synlett 2018, 29, 1937.
[39]
Baudoin, O. Acc. Chem. Res. 2017, 50, 1114.
[40]
Dastbaravardeh, N.; Christakakou, M.; Haider, M.; Schnürch, M. Synthesis 2015, 45, 1421.
[41]
Liu, Y.; You, T.; Wang, H. X.; Tang, Z.; Zhou, C. Y.; Che, C. M. Chem. Soc. Rev. 2020, 49, 5310.
[42]
Gonnard, L.; Guérinot, A.; Cossy, J. Tetrahedron 2019, 75, 145.
[43]
Hou, W.; Yang, Y.; Wu, Y.; Feng, H.; Li, Y.; Zhou, B. Chem. Commun. 2016, 52, 9672.
[44]
Stevens, R. V. In The Total Synthesis of Natural Products, Ed.: Apsimon, J., Wiley, New York, 1977, 3, 489.
[45]
Tang, Y.; Chen, K. Dyes Pigm 1994, 26, 159.
[46]
Sauer, M.; Han, K. T.; Muller, R.; Nord, S.; Schulz, A.; Seeger, S.; Wolfrum, J.; Arden-Jacob, J.; Deltau, G.; Marx, N. J.; Zander, C.; Drexhage, K. H. J. Fluoresc. 1995, 5, 247.
[47]
Vejdelek, Z.; Protiva, M. Collect. Czech. Chem. Commun. 1990, 55, 1290.
[48]
Han, S.; Park, J.; Kim, S.; Lee, S. H.; Sharma, S.; Mishra, N. K.; Jung, Y. H.; Kim, I. S. Org. Lett. 2016, 18, 4666.
[49]
Kim, S.; Han, S.; Park, J.; Sharma, S.; Mishra, N. K.; Oh, H.; Kwak, J. H.; Kim, I. S. Chem. Commun. 2017, 53, 3006.
[50]
Liu, B. X.; Hu, P. J.; Zhou, X. K.; Bai, D. C.; Chang, J. B.; Li, X. W. Org. Lett. 2017, 19, 2086.
[51]
Kumar, R.; Parmar, D.; Gupta, S. S.; Sharma, U. J. Org. Chem. 2020, 85, 1181.
[52]
Huang, L. T.; Fukagawa, S.; Kojima, M.; Yoshino, T.; Matsunaga, S. Org. Lett. 2020, 22, 8256.
[53]
Kumar, R.; Sharma, R.; Kumar, R.; Sharma, U. Org. Lett. 2020, 22, 305.
[54]
Wasa, M.; Engle, K. M.; Yu, J. Q. Isr. J. Chem. 2010, 50, 605.
[55]
Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902.
[56]
Wang, X.; Yu, D. G.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 10280.
[57]
Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. Trans. 1915, 107, 1080.
[58]
Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735.
[59]
Kumar, R.; Parmar, D.; Gupta, S. S.; Chandra, D.; Dhiman, A. K.; Sharma, U. Chem.-Eur. J. 2020, 26, 4396.
[60]
Yuan, C. C.; Tu, G. L.; Zhao, Y. S. Org. Lett. 2017, 19, 356.
[61]
Knecht, T.; Pinkert, T.; Dalton, T.; Lerchen, A.; Glorius, F. ACS Catal. 2018, 9, 1253.
[62]
Lerchen, A.; Knecht, T.; Koy, M.; Ernst, J. B.; Bergander, K.; Daniliuc, C. G.; Glorius, F. Angew. Chem., Int. Ed. 2018, 57, 15248.
[63]
Ghosh, B.; Samanta, R. Chem. Commun. 2019, 55, 6886.
[64]
Sharmoukh, W.; Ko, K. C.; Noh, C.; Lee, J. Y.; Son, S. U. J. Org. Chem. 2010, 75, 6708.
[65]
Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2013, 113, 5595.
[66]
Yu, S. J.; Li, Y. Z.; Kong, L. H.; Zhou, X. K.; Tang, G. D.; Lan, Y.; Li, X. W. ACS Catal. 2016, 6, 7744.
[67]
Burke, J. P.; Bian, Z.; Shaw, S.; Zhao, B.; Goodwin, C. M.; Belmar, J.; Browning, C. F.; Vigil, D.; Friberg, A.; Camper, D. V.; Rossanese, O. W.; Lee, T.; Olejniczak, E. T.; Fesik, S. W. J. Med. Chem. 2015, 58, 3794.
[68]
Kong, L. H.; Zhou, X. K.; Xu, Y. W.; Li, X. W. Org. Lett. 2017, 19, 3644.
[69]
Zhao, H.; Zhou, X.; Li, B.; Liu, X.; Guo, N.; Lu, Z.; Wang, S. J. Org. Chem. 2018, 83, 4153.
[70]
Zhu, Y. Q.; He, J. L.; Niu, Y. X.; Han, T. F.; Zhu, K. ChemistrySelect 2019, 4, 576.
[71]
Li, T.; Liu, C.; Wu, S.; Chen, C.; Zhu, B. Org. Biomol. Chem. 2019, 17, 7679.
[72]
Kong, L. H.; Liu, B. X.; Zhou, X. K.; Wang, F.; Li, X. W. Chem. Commun. 2017, 53, 10326.
[73]
Shan, B. D.; Kang, B. T.; Song, M. Y.; Wang, R.; Chen, G. Z.; Li, C. C.; Zhao, H. Q. Adv. Synth. Catal. 2020, 362, 2541.
[74]
Jiang, Y. Q.; Li, P. F.; Zhao, J.; Liu, B. X.; Li, X. W. Org. Lett. 2020, 22, 7475.
[75]
Hili, R.; Yudin, A. K. Nat. Chem. Biol. 2006, 2, 284.
[76]
Sánchez, C.; Méndez, C.; Salas, J. A. Nat. Prod. Rep. 2006, 23, 1007.
[77]
Kim, J.; Movassaghi, M. Acc. Chem. Res. 2015, 48, 1159.
[78]
Turkmen, Y. E.; Aggarwal, V. K. Science 2014, 343, 33.
[79]
Grabowski, K.; Schneider, G. Curr. Chem. Biol. 2007, 1, 115.
[80]
Wang, J. L.; Zheng, G. F.; Li, X. W. Chem. Commun. 2020, 56, 7809.
[81]
Hu, X. H.; Yang, X. F.; Loh, T. P. ACS Catal. 2016, 6, 5930.
[82]
Yu, S.; Tang, G.; Li, Y.; Zhou, X.; Lan, Y.; Li, X. W. Angew. Chem., Int. Ed. 2016, 55, 8696.
[83]
Jeong, T.; Mishra, N. K.; Dey, P.; Oh, H.; Han, S.; Lee, S. H.; Kim, H. S.; Park, J.; Kim, I. S. Chem. Commun. 2017, 53, 11197.
[84]
Huang, X. L.; Wang, Y.; Lan, J. B.; You, J. S. Angew. Chem., Int. Ed. 2015, 54, 9404.
[85]
Burman, J. S.; Blakey, S. B. Angew. Chem., Int. Ed. 2017, 56, 13666.
[86]
Wang, Y. W.; Liu, H. X.; Li, B.; Wang, B. Q. Adv. Synth. Catal. 2018, 361, 1564.
[87]
Shi, H.; Dixon, D. J. Chem. Sci. 2019, 10, 3733.
[88]
Burman, J. S.; Harris, R.; Farr, C.; Bacsa, J.; Blakey, S. B. ACS Catal. 2019, 9. 5474.
[89]
Wang, H.; Tang, G. D.; Li, X. W. Angew. Chem., Int. Ed. 2015, 54, 13049.
[90]
Fukagawa, S.; Kojima, M.; Yoshino, T.; Matsunaga, S. Angew. Chem., Int. Ed. 2019, 58, 18154.
[91]
Farr, C. M. B.; Kazerouni, A. M.; Park, B.; Poff, C. D.; Won, J.; Sharp, K. R.; Baik, M. H.; Blakey, S. B. J. Am. Chem. Soc. 2020, 142, 13996.
[92]
Cochet, T.; Bellosta, V.; Roche, D.; Ortholand, J. Y.; Greiner, A.; Cossy, J. Chem. Commun. 2012, 48, 10745.
[93]
Tan, X.; Liu, B.; Li, X.; Li, B.; Xu, S.; Song, H.; Wang, B. J. Am. Chem. Soc. 2012, 134, 16163.
[94]
Archambeau, A.; Rovis, T. Angew. Chem., Int. Ed. 2015, 54, 13337.
[95]
Chan, C. M.; Zhou, Z. Y.; Yu, W. Y. Adv. Synth. Catal. 2016, 358, 4067.
[96]
Sun, J. Q.; Wang, K.; Wang, P. Y.; Zheng, G. F.; Li, X. W. Org. Lett. 2019, 21, 4662.
[97]
Zhou, B.; Chen, Z.; Yang, Y.; Ai, W.; Tang, H.; Wu, Y.; Zhu, W.; Li, Y. Angew. Chem., Int. Ed. 2015, 54, 12121.
[98]
Audic, B.; Cramer, N. Org. Lett. 2020, 22, 5030.
[99]
Kondo, Y.; García-Cuadrado, D.; Hartwig, J. F.; Boaen, N. K.; Wagner, N. L.; Hillmyer, M. A. J. Am. Chem. Soc. 2002, 124, 1164.
[100]
Bae, C.; Hartwig, J. F.; Boaen Harris, N. K.; Long, R. O.; Anderson, K. S.; Hillmyer, M. A. J. Am. Chem. Soc. 2005, 127, 767.
[101]
Maity, S.; Karmakar, U.; Samanta, R. Chem. Commun. 2017, 53, 12197.
[102]
Nelson, T. A. F.; Blakey S. B. Angew. Chem., Int. Ed. 2018, 57, 14911.
[103]
Chen, Y. K.; Kang, Y. S.; Xu, H. J.; Zhang, P.; Zhao, J.; Li, T.; Sun, W. Y.; Lu, Y. Org. Lett. 2020, 22, 5390.
[104]
Della-Felice, F.; Zanini, M.; Jie, X.; Tan, E.; Echavarren, A. M. Angew. Chem., Int. Ed. 2021, 60, 5693.
Options
Outlines

/

〈 〉