Citation: Wang Qiang, Gu Qing, You Shu-Li. Recent Progress on Transition-Metal-Catalyzed Asymmetric C-H Bond Functionalization for the Synthesis of Biaryl Atropisomers[J]. Acta Chimica Sinica, ;2019, 77(8): 690-704. doi: 10.6023/A19060222 shu

Recent Progress on Transition-Metal-Catalyzed Asymmetric C-H Bond Functionalization for the Synthesis of Biaryl Atropisomers

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: You Shu-Li, slyou@sioc.ac.cn
Received Date: 19 June 2019
Available Online: 17 August 2019
Fund Project: the National Natural Science Foundation of China 21572250Project supported by the National Natural Science Foundation of China (91856201, 21572250), the Initiative Postdocs Supporting Program (BX20180342) and China Postdoctoral Science Foundation (2019M650092)China Postdoctoral Science Foundation 2019M650092the Initiative Postdocs Supporting Program BX20180342the National Natural Science Foundation of China 91856201

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Axial chirality is of significant importance in chiral molecules. Axially chiral biaryls are existed in numerous natural products and biologically active molecules. Moreover, they have been extensively used as chiral catalysts and chiral ligands in asymmetric catalysis. Due to the importance of these privileged scaffolds, considerable attention has been attracted to develop novel, efficient and practical methods for their asymmetric synthesis by utilizing chiral transition-metal catalysis or chiral organocatalysis. Among those reported elegant achievements, asymmetric C—H bond functionalization reactions are the most concise and efficient methods for the synthesis of axial chiral biaryls in terms of atom and step economies. With the advancement of transition-metal-catalyzed asymmetric C—H bond functionalization reactions, they largely promote the field of asymmetric synthesis of axially chiral biaryls. Recent progress on the development of synthesis of axially chiral biaryls via transition metal (Pd-, Rh-, and Ir-) catalyzed asymmetric C—H bond functionalization reactions are summarized in this review. Those mainly include:Rh-catalyzed enantioselective C(sp²)-H bond alkylation and arylation reactions with the combination of rhodium (I) catalyst precursors and chiral phosphine ligands; Rh-catalyzed enantioselective C(sp²)-H bond alkenylation, arylation and annulation reactions with well-defined chiral rhodium (Ⅲ)-Cp(SCp) complexes; Ir-catalyzed enantioselective C(sp²)-H bond arylation reactions with chiral iridium (Ⅲ)-Cp complex and chiral amino acid as co-catalyst; Pd-catalyzed diastereoselective C(sp²)-H bond alkenylation, iodination, and arylation reactions using chiral p-tolyl sulfoxide auxiliary or menthyl phenylphosphate group as a directing group; Pd-catalyzed intramolecular enantioselective C(sp²)-H bond arylation reaction with Pd(0) catalyst precursors and chiral TADDOL-phosphoramidites; Pd-catalyzed intermolecular enantioselective C(sp²)-H bond iodination, alkenylation, alkynylation, allylation and arylation reactions with Pd(Ⅱ) catalyst precursors and mono-N-protected amino acids (MPAAs). In addition, preparation of varieties of novel axially chiral ligands by utilizing these methods and their applications in catalytic asymmetric reactions are also covered. Meanwhile, applications of these methods as key steps in the synthesis of natural products are also discussed.
- transition metal catalysis,
- asymmetric catalysis,
- asymmetric C—H functionalization,
- axial chirality
1. [1]
  For selected reviews, (a) Chang, J.; Reiner, J.; Xie, J. Chem. Rev. 2005, 105, 4581. (b) Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193. (c) Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563.
2. [2]
  For selected works, see: (a) Wu, Y.-L.; Ferroni, F.; Pieraccini, S.; Schweizer, W. B.; Frank, B. B.; Spada, G. P.; Diederich, F. Org. Biomol. Chem. 2012, 10, 8016. (b) Zhu, Y.-Y.; Wu, X.-D.; Gu, S.-X.; Pu, L. J. Am. Chem. Soc. 2019, 141, 175. For a review: (c) Pu, L. Acc. Chem. Res. 2012, 45, 150.
3. [3]
  (a) Clayden, J.; Moran, W. J.; Edwards, P. J.; LaPlante, S. R. Angew. Chem. Int. Ed. 2009, 48, 6398. (b) LaPlante, S. R.; Edwards, P. J.; Fader, L. D.; Jakalian, A.; Hucke, O. ChemMedChem 2011, 6, 505. (c) Zask, A.; Murphy, J.; Ellestad, G. A. Chirality 2013, 25, 265. (d) Smyth, J. E.; Butler, N. M.; Keller, P. A. Nat. Prod. Rep. 2015, 32, 1562.
4. [4]
  For selected reviews, see: (a) Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999. (b) Brunel, J. M. Chem. Rev. 2007, 107, PR1. (c) Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156. (d) Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047. (e) Min, C.; Seidel, D. Chem. Soc. Rev. 2017, 46, 5889. (f) Wang, Q.; Gu, Q.; You, S.-L. Angew. Chem. Int. Ed. 2019, 58, 6818. For a book, see: (g) Privileged Chiral Ligands and Catalysts, Ed.: Zhou, Q.-L., Wiley-VCH, Weinheim, Germany, 2011.
5. [5]
6. [6]
7. [7]
  Kakiuchi, F.; Le Gendre, P.; Yamada, A.; Ohtaki, H.; Murai, S. Tetrahedron:Asymmetry 2000, 11, 2647. doi: 10.1016/S0957-4166(00)00244-5
8. [8]
  For reviews on asymmetric C-H functionalization, see: (a) Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242. (b) Yang, L.; Huang, H. Catal. Sci. Technol. 2012, 2, 1099. (c) Engle, K. M.; Yu, J.-Q. J. Org. Chem. 2013, 78, 8927. (d) Wencel-Delord, J.; Colobert, F. Chem. Eur. J. 2013, 19, 14010. (e) Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173. (f) Pedroni, J.; Cramer, N. Chem. Commun. 2015, 51, 17647. (g) Newton, C. G.; Wang, S.-G.; Oliveira, C. C.; Cramer, N. Chem. Rev. 2017, 117, 8908. (h) Gao, D.-W.; Gu, Q.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2017, 50, 351; (i) Saint-Denis, T. G.; Zhu, R.-Y.; Chen, G.; Wu, Q.-F.; Yu, J.-Q. Science 2018, 359, 759. For a book, see: (j) Asymmetric Functionalization of C-H Bonds, Ed.: You, S.-L., RSC: Cambridge, UK, 2015.
9. [9]
  Zheng, J.; You, S.-L. Angew. Chem. Int. Ed. 2014, 53, 13244. doi: 10.1002/anie.201408805
10. [10]
  (a) Ye, B.; Cramer, N. Science 2012, 338, 504. (b) Ye, B.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 636. (c) Ye, B.; Donets, P. A.; Cramer, N. Angew. Chem. Int. Ed. 2014, 53, 507. (d) Ye, B.; Cramer, N. Angew. Chem. Int. Ed. 2014, 53, 7896.
11. [11]
  Zheng, J.; Cui, W. J.; Zheng, C.; You, S.-L. J. Am. Chem. Soc. 2016, 138, 5242. doi: 10.1021/jacs.6b02302
12. [12]
  Gre ies, S.; Klauck, F. J. R.; Kim, J. H.; Daniliuc, C. G.; Glorius, F. Angew. Chem. Int. Ed. 2018, 57, 9950. doi: 10.1002/anie.201805680
13. [13]
  Wang, Q.; Cai, Z.-J.; Liu, C.-X.; Gu, Q.; You, S.-L. J. Am. Chem. Soc. 2019, 141, 9504. doi: 10.1021/jacs.9b03862
14. [14]
  Jia, Z. J.; Merten, C.; Gontla, R.; Daniliuc, C. G.; Antonchick, A. P.; Waldmann, H. Angew. Chem. Int. Ed. 2017, 56, 2429. doi: 10.1002/anie.201611981
15. [15]
  For reviews on chiral cyclopentadienyl ligands, see: (a) Ye, B.; Cramer, N. Acc. Chem. Res. 2015, 48, 1308. (b) Newton, C. G.; Kossler, D.; Cramer, N. J. Am. Chem. Soc. 2016, 138, 3935.
16. [16]
  Shan, G.; Flegel, J.; Li, H.; Merten, C.; Ziegler, S.; Antonchick, A. P.; Waldmann, H. Angew. Chem. Int. Ed. 2018, 57, 14250. doi: 10.1002/anie.201809680
17. [17]
  Tian, M.; Bai, D.; Zheng, G.; Chang, J.; Li, X. J. Am. Chem. Soc. 2019, 141, 9527. doi: 10.1021/jacs.9b04711
18. [18]
  Jang, Y. S.; Dieckmann, M.; Cramer, N. Angew. Chem. Int. Ed. 2017, 56, 15088. doi: 10.1002/anie.201708440
19. [19]
  B rner, A. Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications, Vol. 1~3, Wiley-VCH, Weinheim, 2008.
20. [20]
  Cramer, N.; Jang, Y. S.; Wozniak, L.; Pedroni, J. Angew. Chem. Int. Ed. 2018, 57, 12901. doi: 10.1002/anie.201807749
21. [21]
  For reviews: (a) Wencel-Delord, J.; Colobert, F. Synlett 2015, 26, 2644. (b) Tang, K.-X.; Wang, C.-M.; Gao, T.-H.; Chen, L.; Fan, L.; Sun, L.-P. Adv. Synth. Catal. 2019, 361, 26.
22. [22]
  Wesch, T.; Leroux, F. R.; Colobert, F. Adv. Synth. Catal. 2013, 355, 2139. doi: 10.1002/adsc.201300446
23. [23]
  (a) Hazra, C. K.; Dherbassy, Q.; Wencel-Delord, J.; Colobert, F. Angew. Chem. Int. Ed. 2014, 53, 13871. (b) Dherbassy, Q.; Schwertz, G.; Hazra, C. K.; Wesch, T.; Wencel-Delord, J.; Colobert, F. Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 1339.
24. [24]
  Dherbassy, Q.; Schwertz, G.; Chessé, M.; Hazra, C. K.; Wencel-Delord, J.; Colobert, F. Chem. Eur. J. 2016, 22, 1735. doi: 10.1002/chem.201503650
25. [25]
  Dherbassy, Q.; Wencel-Delord, J.; Colobert, F. Tetrahedron 2016, 72, 5238. doi: 10.1016/j.tet.2016.03.060
26. [26]
  Dherbassy, Q.; Djukic, J. P.; Wencel-Delord, J.; Colobert, F. Angew. Chem. Int. Ed. 2018, 57, 4668. doi: 10.1002/anie.201801130
27. [27]
  (a) Ma, Y. N.; Zhang, H.-Y.; Yang, S.-D. Org. Lett. 2015, 17, 2034. For reviews, see: (b) Ma, Y. N.; Li, S. X.; Yang, S.-D. Acc. Chem. Res. 2017, 50, 1480. (c) Zhang, Z.; Dixneuf, P. H.; Soule, J. F. Chem. Commun. 2018, 54, 7265.
28. [28]
  Albicker, M., R; Cramer, N. Angew. Chem. Int. Ed. 2009, 48, 9139. doi: 10.1002/anie.200905060
29. [29]
  He, C.; Hou, M.; Zhu, Z.; Gu, Z. ACS Catal. 2017, 7, 5316. doi: 10.1021/acscatal.7b01855
30. [30]
  Newton, C. G.; Braconi, E.; Kuziola, J.; Wodrich, M. D.; Cramer, N. Angew. Chem. Int. Ed. 2018, 57, 11040. doi: 10.1002/anie.201806527
31. [31]
  Yamaguchi, K.; Yamaguchi, J.; Studer, A.; Itami, K. Chem. Sci. 2012, 3, 2165. doi: 10.1039/c2sc20277h
32. [32]
  Yamaguchi, K.; Kondo, H.; Yamaguchi, J.; Itami, K. Chem. Sci. 2013, 4, 3753. doi: 10.1039/c3sc51206a
33. [33]
  Nishimoto, Y.; Kondo, H.; Yamaguchi, K.; Yokogawa, D.; Yamaguchi, J.; Itami, K.; Irle, S. J. Org. Chem. 2017, 82, 4900. doi: 10.1021/acs.joc.6b02675
34. [34]
  Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem. Int. Ed. 2008, 47, 4882. doi: 10.1002/anie.200801030
35. [35]
  Gao, D.-W.; Gu, Q.; You, S.-L. ACS Catal. 2014, 4, 2741. doi: 10.1021/cs500813z
36. [36]
  Li, S. X.; Ma, Y.-N.; Yang, S.-D. Org. Lett. 2017, 19, 1842. doi: 10.1021/acs.orglett.7b00608
37. [37]
  Zhang, F.-L.; Hong, K.; Li, T. J.; Park, H.; Yu, J.-Q. Science 2016, 351, 252. doi: 10.1126/science.aad7893
38. [38]
  Yao, Q.-J.; Zhang, S.; Zhan, B.-B.; Shi, B.-F. Angew. Chem. Int. Ed. 2017, 56, 6617. doi: 10.1002/anie.201701849
39. [39]
  Fan, J.; Yao, Q.-J.; Liu, Y.-H.; Liao, G.; Zhang, S.; Shi, B.-F. Org. Lett. 2019, 21, 3352. doi: 10.1021/acs.orglett.9b01099
40. [40]
  Liao, G.; Yao, Q.-J.; Zhang, Z.-Z.; Wu, Y.-J.; Huang, D. Y.; Shi, B.-F. Angew. Chem. Int. Ed. 2018, 57, 3661. doi: 10.1002/anie.201713106
41. [41]
  Zhang, S.; Yao, Q.-J.; Liao, G.; Li, X.; Li, H.; Chen, H.-M.; Hong, X.; Shi, B.-F. ACS Catal. 2019, 9, 1956. doi: 10.1021/acscatal.8b04870
42. [42]
  Liao, G.; Li, B.; Chen, H.-M.; Yao, Q. J.; Xia, Y. N.; Luo, J.; Shi, B.-F. Angew. Chem. Int. Ed. 2018, 57, 17151. doi: 10.1002/anie.201811256
43. [43]
  Liao, G.; Chen, H.-M.; Xia, Y.-N.; Li, B.; Yao, Q.-J.; Shi, B.-F. Angew. Chem. Int. Ed. 2019, DOI:10.1002/anie.201906700. doi: 10.1002/anie.201906700
44. [44]
  Wen, W.; Chen, L.; Luo, M.-J.; Zhang, Y.; Chen, Y.-C.; Ouyang, Q.; Guo, Q.-X. J. Am. Chem. Soc. 2018, 140, 9774. doi: 10.1021/jacs.8b06676
45. [45]
  Luo, J.; Zhang, T.; Wang, L.; Liao, G.; Yao, Q.-J.; Wu, Y.-J.; Zhan, B.-B.; Lan, Y.; Lin, X.-F.; Shi, B.-F. Angew. Chem. Int. Ed. 2019, 58, 6708. doi: 10.1002/anie.201902126
46. [46]
  Sun, Q.-Y.; Ma, W.-Y.; Yang, K.-F.; Cao, J.; Zheng, Z.-J.; Xu, Z.; Cui, Y.-M.; Xu, L.-W. Chem. Commun. 2018, 54, 10706. doi: 10.1039/C8CC05555F
47. [47]
  Li, H.; Yan, X.; Zhang, J.; Guo, W.; Jiang, J.; Wang, J. Angew. Chem. Int. Ed. 2019, 58, 6732. doi: 10.1002/anie.201901619
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