REVIEWS

Research Progress of Amino Acids as Transient Directing Groups in C—H Bond Activation Reactions

  • Sifan Dong ,
  • Haolong Li ,
  • Yuan Qin ,
  • Shiming Fan ,
  • Shouxin Liu
Expand
  • State Key Laboratory Breeding Base-Hebei Province Key Laboratory of Molecular Chemistry for Drug, Hebei University of Science and Technology, Shijiazhuang 050018

Received date: 2022-12-09

  Revised date: 2023-02-03

  Online published: 2023-03-07

Supported by

National Natural Science Foundation of China(21978067); Natural Science Foundation of Hebei Province(H2020208030); the Open Funding Project of the Hebei Province Key Laboratory of Molecular Chemistry for Drug(2022PT03)

Abstract

In recent years, the transient directing group (TDG)-based strategy of C—H activation has attracted significant attention. Compared with the typical C—H activation reactions, TDG-assisted C—H activation does not require external pre-installation and post-removal steps of directing groups, which significantly improve the atom and step economy. Amino acid-based TDGs for C—H activation have achieved significant successes among the known TDGs. Amino acids have the advantages including low cost, widely existing and diverse structures. The site selectivity of C—H activation can be controlled by using α- or β-amino acids. By using the inherent chirality of amino acids, the stereo-selectivity of reactions can be realized. The research progress of transition-metal-catalyzed C—H bond activation and functionalization with amino acids as TDGs in recent years is summarized, which is classified according to the type of amino acids for C—H activation reactions of various substrates. Finally, the limitations of previous works and perspectives on this cutting-edge area are also described.

Cite this article

Sifan Dong , Haolong Li , Yuan Qin , Shiming Fan , Shouxin Liu . Research Progress of Amino Acids as Transient Directing Groups in C—H Bond Activation Reactions[J]. Chinese Journal of Organic Chemistry, 2023 , 43(7) : 2351 -2367 . DOI: 10.6023/cjoc202212012

References

[1]
Yi, H.; Zhang, G.; Wang, H.; Huang, Z.; Wang, J.; Singh, A. K.; Lei, A. Chem. Rev. 2017, 117, 9016.
[2]
He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J.-Q. Chem. Rev. 2017, 117, 8754.
[3]
Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247.
[4]
Liu, J.; Chen, G.; Tan, Z. Adv. Synth. Catal. 2016, 358, 1174.
[5]
Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976.
[6]
Wencel-Delord, J.; Droege, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740.
[7]
Aspin, S.; Goutierre, A.-S.; Larini, P.; Jazzar, R.; Baudoin, O. Angew. Chem., Int. Ed. 2012, 51, 10808.
[8]
Abrams, D. J.; Provencher, P. A.; Sorensen, E. J. Chem. Soc. Rev. 2018, 47, 8925.
[9]
Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879.
[10]
Godula, K.; Sames, D. Science 2006, 312, 67.
[11]
Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960.
[12]
Hoshiya, N.; Takenaka, K.; Shuto, S.; Uenishi, J.-I. Org. Lett. 2016, 18, 48.
[13]
Jacob, C.; Maes, B. U. W.; Evano, G. Chem.-Eur. J. 2021, 27, 13899.
[14]
Sun, H.; Guimond, N.; Huang, Y. Org. Biomol. Chem. 2016, 14, 8389.
[15]
Zhao, Q.; Poisson, T.; Pannecoucke, X.; Besset, T. Synthesis 2017, 49, 4808.
[16]
Ghosh, M.; De Sarkar, S. Asian J. Org. Chem. 2018, 7, 1236.
[17]
Rasheed, O. K.; Sun, B. ChemistrySelect 2018, 3, 5689.
[18]
Bhattacharya, T.; Pimparkar, S.; Maiti, D. RSC Adv. 2018, 8, 19456.
[19]
Niu, B.; Yang, K.; Lawrence, B.; Ge, H. ChemSusChem 2019, 12, 2955.
[20]
Liao, G.; Zhang, T.; Lin, Z.-K.; Shi, B.-F. Angew. Chem., Int. Ed. 2020, 59, 19773.
[21]
Lapuh, M. I.; Mazeh, S.; Besset, T. ACS Catal. 2020, 10, 12898.
[22]
Zu, B.; Guo, Y.; Ke, J.; He, C. Synthesis 2021, 53, 2029.
[23]
Dutta, U.; Maiti, S.; Bhattacharya, T.; Maiti, D. Science 2021, 372, 5992.
[24]
Wu, Y.; Shi, B.-F. Chin. J. Org. Chem. 2020, 40, 3517 (in Chinese).
[24]
(吴勇杰, 史炳锋, 有机化学, 2020, 40, 3517.)
[25]
Vautravers, N. R.; Regent, D. D.; Breit, B. Chem. Commun. 2011, 47, 6635.
[26]
Beletskiy, E. V.; Sudheer, C.; Douglas, C. J. J. Org. Chem. 2012, 77, 5884.
[27]
Wang, X.; Song, S.; Jiao, N. Chin. J. Chem. 2018, 36, 213.
[28]
Li, F.; Zhou, Y.; Yang, H.; Wang, Z.; Yu, Q.; Zhang, F.-L. Org. Lett. 2019, 21, 3692.
[29]
Huang, J.; Ding, J.; Ding, T.-M.; Zhang, S.; Wang, Y.; Sha, F.; Zhang, S.-Y.; Wu, X.-Y.; Li, Q. Org. Lett. 2019, 21, 7342.
[30]
Higham, J. I.; Bull, J. A. Org. Biomol. Chem. 2020, 18, 7291.
[31]
Zhang, F.-L.; Hong, K.; Li, T.-J.; Park, H.; Yu, J.-Q. Science 2016, 351, 252.
[32]
Tang, M.; Yu, Q.; Wang, Z.; Zhang, C.; Sun, B.; Yi, Y.; Zhang, F.-L. Org. Lett. 2018, 20, 7620.
[33]
Xu, J.; Liu, Y.; Wang, Y.; Li, Y.; Xu, X.; Jin, Z. Org. Lett. 2017, 19, 1562.
[34]
Thrimurtulu, N.; Dey, A.; Singh, A.; Pal, K.; Maiti, D.; Volla, C. M. R. Adv. Synth. Catal. 2019, 361, 1441.
[35]
Singh, A.; Dey, A.; Pal, K.; Dash, O. P.; Volla, C. M. R. Org. Lett. 2022, 24, 1941.
[36]
Liu, X.-H.; Park, H.; Hu, J.-H.; Hu, Y.; Zhang, Q.-L.; Wang, B.-L.; Sun, B.; Yeung, K.-S.; Zhang, F.-L.; Yu, J.-Q. J. Am. Chem. Soc. 2017, 139, 888.
[37]
Wang, D.-Y.; Guo, S.-H.; Pan, G.-F.; Zhu, X.-Q.; Gao, Y.-R.; Wang, Y.-Q. Org. Lett. 2018, 20, 1794.
[38]
Hoshiya, N.; Kobayashi, T.; Arisawa, M.; Shuto, S. Org. Lett. 2013, 15, 6202.
[39]
Yang, X.; Shan, G.; Yang, Z.; Huang, G.; Dong, G.; Sheng, C.; Rao, Y. Chem. Commun. 2017, 53, 1534.
[40]
Cheng, J.-T.; Xiao, L.-J.; Qian, S.-Q.; Zhuang, Z.; Liu, A.; Yu, J.-Q. Angew. Chem., Int. Ed. 2022, 61, e202117233.
[41]
Ding, M.-R.; Hua, W.-K.; Liu, M.; Zhang, F.-Z. Org. Lett. 2020, 22, 7419.
[42]
Li, Y.-H.; Ouyang, Y.; Chekshin, N.; Yu, J.-Q. J. Am. Chem. Soc. 2022, 144, 4727.
[43]
Liu, M.; Sun, J.; Erbay, T. G.; Ni, H.-Q.; Martin-Montero, R.; Liu, P.; Engle, K. M. Angew. Chem., Int. Ed. 2022, 61, e202203624.
[44]
Kong, J.-H.; Jiang, Z.-J.; Xu, J.-Y.; Li, Y.; Cao, H.; Ding, Y.-N.; Tang, B.-C.; Chen, J.; Gao, Z.-H. J. Org. Chem. 2021, 86, 13350.
[45]
Yang, K.; Li, Q.; Liu, Y.-B.; Li, G.-G.; Ge, H.-B. J. Am. Chem. Soc. 2016, 138, 12775.
[46]
Zhang, X.-L.; Pan, G.-F.; Zhu, X.-Q.; Guo, R.-L.; Gao, Y.-R.; Wang, Y.-Q. Org. Lett. 2019, 21, 2731.
[47]
Guan, Z.; Chen, S.-W.; Huang, Y.; Yao, H.-Q. Org. Lett. 2019, 21, 3959.
[48]
Higham, J. I.; Bull, J. A. Angew. Chem., Int. Ed. 2022, 61, e202202933.
[49]
Hong, K.; Park, H.; Yu, J.-Q. ACS Catal. 2017, 7, 6938.
[50]
Chen, X.-Y.; Ozturk, S.; Sorensen, E. J. Org. Lett. 2017, 19, 1140.
[51]
Park, H.; Verma, P.; Hong, K.; Yu, J.-Q. Nat. Chem. 2018, 10, 755.
[52]
Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193.
[53]
Canac, Y.; Chauvin, R. Eur. J. Inorg. Chem. 2010, 16, 2325.
[54]
Wencel-Delord, J.; Panossian, A.; Leroux, F. R.; Colobert, F. Chem. Soc. Rev. 2015, 44, 3418.
[55]
Xu, G.-Q.; Fu, W.-Z.; Liu, G.-D.; Senanayake, C. H.; Tang, W.-J. J. Am. Chem. Soc. 2014, 136, 570.
[56]
Yao, Q.-J.; Zhang, S.; Zhan, B.-B.; Shi, B.-F. Angew. Chem., Int. Ed. 2017, 56, 6617.
[57]
Fan, J.; Yao, Q.-J.; Liu, Y.-H.; Liao, G.; Zhang, S.; Shi, B.-F. Org. Lett. 2019, 21, 3352.
[58]
Liao, G.; Yao, Q.-J.; Zhang, Z.-Z.; Wu, Y.-J.; Huang, D.-Y.; Shi, B.-F. Angew. Chem., Int. Ed. 2018, 57, 3661.
[59]
Xu, J.-C.; Liu, Y.; Zhang, J.-L.; Xu, X.-H.; Jin, Z. Chem. Commun. 2018, 54, 689.
[60]
Zhang, J.-T.; Fan, J.; Guo, Z.-Y.; Wu, Y.-H.; Wu, J.-P.; Xie, M.-H. Adv. Synth. Catal. 2022, 364, 3589.
[61]
Oxtoby, L. J.; Li, Z.-Q.; Tran, V. T.; Erbay, T. G.; Deng, R.; Liu, P.; Engle, K. M. Angew. Chem., Int. Ed. 2020, 59, 8885.
[62]
Xiao, L.-J.; Hong, K.; Luo, F.; Hu, L.; Ewing, W. R.; Yeung, K.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2020, 59, 9594.
Outlines

/