Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(21): 4734-4752
DOI: 10.1055/a-1677-5870

special topic

Asymmetric C–H Functionalization

Recent Advances on Transition-Metal-Catalyzed Asymmetric C–H Arylation Reactions

Mingliang Li

^aDepartment of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055, P. R. of China

,

Jun Wang ∗

^aDepartment of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055, P. R. of China

^bDepartment of Chemistry, Hong Kong Baptist University, Kowloon, Hong Kong, China

› Institutsangaben

Alle Artikel dieser Rubrik

Abstract

Transition-metal-catalyzed asymmetric C–H functionalization has become a powerful strategy to synthesize complex chiral molecules. Recently, catalytic enantioselective C–H arylation has attracted great interest from organic chemists to construct aryl-substituted chiral compounds. In this short review, we highlight recent advances in asymmetric C–H arylation from 2019 to late 2021, including enantioselective C(sp²)–H arylation to construct axial or planar chiral compounds, and enantioselective C(sp³)–H arylation to introduce central chirality via desymmetrization of the methyl group or methylene C–H activation. These processes proceed with palladium, rhodium, iridium, nickel, or copper catalysts, and utilize aryl halides, boron, or diazo derivatives as arylation reagents.

1 Introduction

2 Transition-Metal-Catalyzed Asymmetric C(sp²)–H Arylation

2.1 Chelation-Assisted Asymmetric C(sp²)–H Arylation for the Construction of Atropisomer

2.2 Chelation-Assisted Asymmetric C(sp²)–H Arylation for the Construction of Planar Chiral Compounds

2.3 Chelation-Assisted Asymmetric C(sp²)–H Arylation and Axial-to-Central Chirality Transfer for the Construction of Spirocycles

2.4 Other Asymmetric C(sp²)–H Arylation Reactions

3 Transition-Metal-Catalyzed Asymmetric C(sp³)–H Arylation

3.1 Chelation-Assisted Enantioselective C(sp³)–H Arylation through Desymmetrization

3.2 Chelation-Assisted Enantioselective Methylene C(sp³)–H Arylation

3.3 Other Asymmetric C(sp³)–H Arylations

4 Conclusion and Outlook

Key words

Key words

C–H bond functionalization - transition-metal catalysis - asymmetric C–H activation - C(sp²)–H arylation - C(sp³)–H arylation - arylation - chiral ligands

References

For selected reviews, see:

1a Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
1b Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236
1c Dong Z, Ren Z, Thompson SJ, Xu Y, Dong G. Chem. Rev. 2017; 117: 9333
1d Park Y, Kim Y, Chang S. Chem. Rev. 2017; 117: 9247
1e Leitch JA, Frost CG. Chem. Soc. Rev. 2017; 46: 7145
1f He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
1g Chu JC. K, Rovis T. Angew. Chem. Int. Ed. 2018; 57: 62
1h Gandeepan P, Ackermann L. Chem 2018; 4: 199

For selected reviews, see:

2a Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
2b Wencel-Delord J, Glorius F. Nat. Chem. 2013; 5: 369
2c Ackermann L. Org. Process Res. Dev. 2015; 19: 260
2d Seki M. Org. Process Res. Dev. 2016; 20: 867
2e Basu D, Kumar S, Sai Sudhir V, Bandichhor R. J. Chem. Sci. 2018; 130: 71
2f Baudoin O. Angew. Chem. Int. Ed. 2020; 59: 17798

3 Hartwig JF, Larsen MA. ACS Cent. Sci. 2016; 2: 281

For selected reviews, see:

4a Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936
4b Rouquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
4c Daugulis O, Roane J, Tran LD. Acc. Chem. Res. 2015; 48: 1053
4d Dey A, Maity S, Maiti D. Chem. Commun. 2016; 52: 12398
4e Dey A, Sinha SK, Achar TK, Maiti D. Angew. Chem. Int. Ed. 2019; 58: 10820
4f Meng G, Lam NY. S, Lucas EL, Saint-Denis TG, Verma P, Chekshin N, Yu J.-Q. J. Am. Chem. Soc. 2020; 142: 10571

For selected reviews, see:

5a Moir M, Danon JJ, Reekie TA, Kassiou M. Expert Opin. Drug Discovery 2019; 14: 1137
5b Börgel J, Ritter T. Chem 2020; 6: 1877
5c Kelly CB, Padilla-Salinas R. Chem. Sci. 2020; 11: 10047

6 Carey JS, Laffan D, Thomson C, Williams MT. Org. Biomol. Chem. 2006; 4: 2337

For selected reviews, see:

7a Zheng C, You S.-L. RSC Adv. 2014; 4: 6173
7b Pellissier H, Clavier H. Chem. Rev. 2014; 114: 2775
7c Wang F, Chen P, Liu G. Acc. Chem. Res. 2018; 51: 2036
7d Pellissier H. Coord. Chem. Rev. 2019; 386: 1

For selected examples, see:

8a Groves JT, Viski P. J. Am. Chem. Soc. 1989; 111: 8537
8b Burg F, Breitenlechner S, Jandl C, Bach T. Chem. Sci. 2020; 11: 2121

For selected examples, see:

9a DeAngelis A, Shurtleff VM, Dmitrenko O, Fox JM. J. Am. Chem. Soc. 2011; 133: 1650
9b Liao K, Negretti S, Musaev DG, Bacsa J, Davies HM. L. Nature 2016; 533: 230

For selected reviews, see:

10a Newton CG, Wang S.-G, Oliveira CC, Cramer N. Chem. Rev. 2017; 117: 8908
10b Saint-Denis TG, Zhu R.-Y, Chen G, Wu Q.-F, Yu J.-Q. Science 2018; 359: eaao4798
10c Diesel J, Cramer N. ACS Catal. 2019; 9: 9164
10d Shao Q, Wu K, Zhuang Z, Qian S, Yu J.-Q. Acc. Chem. Res. 2020; 53: 833
10e Thongpaen J, Manguin R, Baslé O. Angew. Chem. Int. Ed. 2020; 59: 10242
10f Yang K, Song M, Liu H, Ge H. Chem. Sci. 2020; 11: 12616
10g Liao G, Zhang T, Lin Z.-K, Shi B.-F. Angew. Chem. Int. Ed. 2020; 59: 19773
10h Liu C.-X, Gu Q, You S.-L. Trends Chem. 2020; 2: 737
10i Achar TK, Maiti S, Jana S, Maiti D. ACS Catal. 2020; 10: 13748
10j Liu W, Ke J, He C. Chem. Sci. 2021; 12: 10972
10k Liu C.-X, Zhang W.-W, Yin S.-Y, Gu Q, You S.-L. J. Am. Chem. Soc. 2021; 143: 14025

11 Wang Q, Cai Z.-J, Liu C.-X, Gu Q, You S.-L. J. Am. Chem. Soc. 2019; 141: 9504
12 Wang Q, Zhang W.-W, Song H, Wang J, Zheng C, Gu Q, You S.-L. J. Am. Chem. Soc. 2020; 142: 15678
13 Feng J, Gu Z. SynOpen 2021; 5: 68
14 Jin L, Yao Q.-J, Xie P.-P, Li Y, Zhan B.-B, Han Y.-Q, Hong X, Shi B.-F. Chem 2020; 6: 497
15 Yang C, Wu T.-R, Li Y, Wu B.-B, Jin R.-X, Hu D.-D, Li Y.-B, Bian K.-J, Wang X.-S. Chem. Sci. 2021; 12: 3726
16 Pan C, Yin S.-Y, Wang S.-B, Gu Q, You S.-L. Angew. Chem. Int. Ed. 2021; 60: 15510
17 Woźniak Ł, Cramer N. Angew. Chem. Int. Ed. 2021; 60: 18532
18 Cai Z.-J, Liu C.-X, Gu Q, Zheng C, You S.-L. Angew. Chem. Int. Ed. 2019; 58: 2149
19 Cai Z.-J, Liu C.-X, Wang Q, Gu Q, You S.-L. Nat. Commun. 2019; 10: 4168
20 Liu C.-X, Cai Z.-J, Wang Q, Wu Z.-J, Gu Q, You S.-L. CCS Chem. 2020; 2: 642
21 Kong L, Han X, Liu S, Zou Y, Lan Y, Li X. Angew. Chem. Int. Ed. 2020; 59: 7188
22 Batuecas M, Luo J, Gergelitsová I, Krämer K, Whitaker D, Vitorica-Yrezabal IJ, Larrosa I. ACS Catal. 2019; 9: 5268
23 Nguyen Q.-H, Guo S.-M, Royal T, Baudoin O, Cramer N. J. Am. Chem. Soc. 2020; 142: 2161
24 Savary D, Baudoin O. Angew. Chem. Int. Ed. 2021; 60: 5136
25 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
26 Saint-Denis TG, Lam NY. S, Chekshin N, Richardson PF, Chen JS, Elleraas J, Hesp KD, Schmitt DC, Lian Y, Huh CW, Yu J.-Q. ACS Catal. 2021; 11: 9738
27 Jerhaoui S, Djukic J.-P, Wencel-Delord J, Colobert F. ACS Catal. 2019; 9: 2532
28 Zhuang Z, Yu J.-Q. J. Am. Chem. Soc. 2020; 142: 12015
29 Han Y.-Q, Yang X, Kong K.-X, Deng Y.-T, Wu L.-S, Ding Y, Shi B.-F. Angew. Chem. Int. Ed. 2020; 59: 20455
30 Han Y.-Q, Zhang Q, Yang X, Jiang M.-X, Ding Y, Shi B.-F. Org. Lett. 2021; 23: 97
31 Yang X, Jiang M.-X, Zhou T, Han Y.-Q, Xu X.-T, Zhang K, Shi B.-F. Chem. Commun. 2021; 57: 5562
32 Xiao L.-J, Hong K, Luo F, Hu L, Ewing WR, Yeung K.-S, Yu J.-Q. Angew. Chem. Int. Ed. 2020; 59: 9594
33 Zhang W, Wu L, Chen P, Liu G. Angew. Chem. Int. Ed. 2019; 58: 6425
34 Cheng X, Lu H, Lu Z. Nat. Commun. 2019; 10: 3549
35 Kong W.-X, Xie S.-J, Cao C.-Y.-Z, Zhang C.-W, Wang C, Duan W.-L. Chem. Commun. 2020; 56: 2292
36 Melot R, Zuccarello M, Cavalli D, Niggli N, Devereux M, Bgrgi T, Baudoin O. Angew. Chem. Int. Ed. 2021; 60: 7245