RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2022; 54(21): 4795-4801
DOI: 10.1055/a-1662-7096
DOI: 10.1055/a-1662-7096
special topic
Asymmetric C–H Functionalization
Asymmetric C–H Functionalization Enabled by Pd/Chiral Phosphoric Acid Combined Catalysis
We are grateful for financial support from the Ministry of Science and Technology of the People’s Republic of China (2015CB856600), the National Natural Science Foundation of China (NSFC, 21831007 and 21672197) and Youth Innovation Promotion Association of the Chinese Academy of Sciences is gratefully acknowledged.
Abstract
Over the past decade, the combination of chiral phosphoric acid and palladium catalysis has emerged as a robust strategy to accomplish the regio- and stereoselective functionalization of inactive C–H bonds, enabling access to various types of chirality (central, planar, and axial). This review article describes the origin and advances in the asymmetric functionalization of allylic C–H, C(sp2)–H, and C(sp3)–H bonds enabled by chiral phosphoric acid and palladium combined catalysis.
1 Introduction
2.1 Enantioselective Allylic C–H Functionalization
2.2 Enantioselective Non-allylic C(sp3)–H Functionalization
2.3 Enantioselective C(sp2)–H Functionalization
3 Conclusion
Key words
asymmetric catalysis - palladium catalysis - C–H activation - chiral phosphoric acid - combined catalysisPublikationsverlauf
Eingereicht: 07. September 2021
Angenommen nach Revision: 06. Oktober 2021
Accepted Manuscript online:
06. Oktober 2021
Artikel online veröffentlicht:
22. November 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Gutekunst WR, Baran PS. Chem. Soc. Rev. 2011; 40: 1976
- 2 Zheng C, You SL. RSC Adv. 2014; 4: 6173
- 3a Newton CG, Wang S.-G, Oliveira CC, Cramer N. Chem. Rev. 2017; 117: 8908
- 3b Saint-Denis TG, Zhu R.-Y, Chen G, Wu Q.-F, Yu J.-Q. Science 2018; 359: eaao4798
- 3c Tran VT, Nimmagadda SK, Liu M, Engle KM. Org. Biomol. Chem. 2020; 18: 618
- 4a Du Y, Su W, Huang Y, Gao Y, Shen H, Hong M. Sci. Sin. Chim. 2021; 51: 123
- 4b Zhang Q, Shi BF. Acc. Chem. Res. 2021; 54: 2750
- 5a Shi B.-F, Maugel N, Zhang Y.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2008; 47: 4882
- 5b Sokolov VI. J. Organomet. Chem. 1995; 500: 299
- 6a Akiyama T, Itoh J, Yokota K, Fuchibe K. Angew. Chem. Int. Ed. 2004; 43: 1566
- 6b Uraguchi D, Terada M. J. Am. Chem. Soc. 2004; 126: 5356
- 6c Yu J, Shi F, Gong LZ. Acc. Chem. Res. 2011; 44: 1156
- 6d Wu H, He YP, Shi F. Synthesis 2015; 47: 1990
- 7 Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047
- 8a Qi X, Chen P, Liu G. Sci. China Chem. 2015; 58: 1249
- 8b Wang R, Luan Y, Ye M. Chin. J. Chem. 2019; 37: 720
- 8c Nelson TA. F, Hollerbach MR, Blakey SB. Dalton Trans. 2020; 49: 13928
- 9 Wang P.-S, Gong L.-Z. Acc. Chem. Res. 2020; 53: 2841
- 10 Chai Z, Rainey TJ. J. Am. Chem. Soc. 2012; 134: 3615
- 11 Jindal G, Sunoj RB. J. Am. Chem. Soc. 2014; 136: 15998
- 12a Mukherjee S, List B. J. Am. Chem. Soc. 2007; 129: 11336
- 12b Jiang G, List B. Angew. Chem. Int. Ed. 2011; 50: 9471
- 12c Mahlau M, List B. Angew. Chem. Int. Ed. 2013; 52: 518
- 13 Wang P.-S, Lin H.-C, Zhai Y.-J, Han Z.-Y, Gong L.-Z. Angew. Chem. Int. Ed. 2014; 53: 12218
- 14 Zhou X.-L, Su Y.-L, Wang P.-S, Gong L.-Z. Acta Chim. Sin. 2018; 76: 857
- 15 Tao Z.-L, Zhang W.-Q, Chen D.-F, Adele A, Gong L.-Z. J. Am. Chem. Soc. 2013; 135: 9255
- 16 Lin H.-C, Wang P.-S, Tao Z.-L, Chen Y.-G, Han Z.-Y, Gong L.-Z. J. Am. Chem. Soc. 2016; 138: 14354
- 17 Fan L.-F, Wang P.-S, Gong L.-Z. Org. Lett. 2019; 21: 6720
- 18a Wu X, Li M.-L, Gong L.-Z. Acta Chim. Sin. 2013; 71: 1091
- 18b Chen D.-F, Han Z.-Y, Zhou X.-L, Gong L.-Z. Acc. Chem. Res. 2014; 47: 2365
- 18c Han Z.-Y, Gong L.-Z. Prog. Chem. 2018; 30: 505
- 18d Wang P.-S, Chen D.-F, Gong L.-Z. Top. Curr. Chem. 2019; 378: 9
- 19 Tao Z.-L, Li X.-H, Han Z.-Y, Gong L.-Z. J. Am. Chem. Soc. 2015; 137: 4054
- 20 Li L.-L, Tao Z.-L, Han Z.-Y, Gong L.-Z. Org. Lett. 2017; 19: 102
- 21 Engle KM, Yu J.-Q. J. Org. Chem. 2013; 78: 8927
- 22 Yan S.-B, Zhang S, Duan W.-L. Org. Lett. 2015; 17: 2458
- 23 Wang H, Tong HR, He G, Chen G. Angew. Chem. Int. Ed. 2016; 55: 15387
- 24 Yan S.-Y, Han Y.-Q, Yao Q.-J, Nie X.-L, Liu L, Shi B.-F. Angew. Chem. Int. Ed. 2018; 57: 9093
- 25 Han Y.-Q, Zhang Q, Yang X, Jiang M.-X, Ding Y, Shi B.-F. Org. Lett. 2021; 23: 97
- 26 Smalley AP, Cuthbertson JD, Gaunt MJ. J. Am. Chem. Soc. 2017; 139: 1412
- 27 Jain P, Verma P, Xia G, Yu J.-Q. Nat. Chem. 2016; 9: 140
- 28 Jiang H.-J, Zhong X.-M, Liu Z.-Y, Geng R.-L, Li Y.-Y, Wu Y.-D, Zhang X, Gong L.-Z. Angew. Chem. Int. Ed. 2020; 59: 12774
- 29 Zhang S, Lu J, Ye J, Duan W.-L. Chin. J. Org. Chem. 2016; 36: 752
- 30 Yang L, Melot R, Neuburger M, Baudoin O. Chem. Sci. 2017; 8: 1344
- 31 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
- 32 Zhan B.-B, Wang L, Luo J, Lin X.-F, Shi B.-F. Angew. Chem. Int. Ed. 2020; 59: 3568
- 33 Zhan B.-B, Jia ZS, Luo J, Jin L, Lin X.-F, Shi B.-F. Org. Lett. 2020; 22: 9693
- 34 Jin L, Zhang P, Li Y, Yu X, Shi B.-F. J. Am. Chem. Soc. 2021; 143: 12335
For early stoichiometric example, please see: