Half-Sandwich d6-Metal (CoIII, RhIII, IrIII, RuII)-Catalyzed Enantioselective C–H Activation

Pu-Fan Qian; Jun-Yi Li; Yi-Bo Zhou; Tao Zhou; Bing-Feng Shi

doi:10.1055/a-2167-8298

SynOpen, Table of Contents

CC BY 4.0 · SynOpen 2023; 07(04): 466-485
DOI: 10.1055/a-2167-8298

graphical review

Half-Sandwich d⁶-Metal (Co^III, Rh^III, Ir^III, Ru^II)-Catalyzed Enantioselective C–H Activation

Pu-Fan Qian ‡

^aCenter of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China

,

Jun-Yi Li‡

^aCenter of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China

,

Yi-Bo Zhou‡

^aCenter of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China

,

Tao Zhou∗

^aCenter of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China

,

Bing-Feng Shi ∗

^aCenter of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China

^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan, 450001, P. R. of China

^cSchool of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, P. R. of China

^dCollege of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China

^eSchool of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

Transition-metal-catalyzed enantioselective C–H activation provides a straightforward strategy to synthesize chiral molecules from readily available sources. In this graphical review, we summarize the progress on half-sandwich d⁶-metal (Co^III, Rh^III, Ir^III, Ru^II)-catalyzed enantioselective C–H functionalization reactions. The review is categorized according to the type of metal catalyst and chiral ligand employed. Representative enantio-determining models and catalytic cycles are presented.

Keywords

enantioselectivity - C–H activation - half-sandwich - cobalt - rhodium - iridium - ruthenium - chiral carboxylic acid

Full Text

References

References
1 Shi B.-F, Maugel N, Zhang Y.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2008; 47: 4882

During the preparation of this graphical review, several reports on this topic appeared highlighting the importance of these chiral catalysts, see:

2a Huang L.-T, Kitakawa Y, Yamada K, Kamiyama F, Kojima M, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed. 2023; 62: e202305480
2b Yang H, Zhang R, Zhang S.-Z, Gu Q, You S.-L. ACS. Catal. 2023; 13: 8838
2c Yang H, Yang Z.-Q, Zhang S.-Z, Zhang W.-W, Gu Q, You S.-L. Sci. China Chem. 2023; 66 in press; DOI: 10.1007/s11426 -023-1637-8
2d Zhang S.-Z, Zhang W.-W, Yang H, Gu Q, You S.-L. Chin. J. Org. Chem. 2023; 43: 2926
2e Zheng Y, Zhang W.-Y, Gu Q, Zheng C, You S.-L. Nat. Commun. 2023; 14: 1094
2f Zhang W.-W, Wang Q, Zhang S.-Z, Zheng C, You S.-L. Angew. Chem. Int. Ed. 2023; 62: e202214460
2g Guo W, Pang X, Jiang J, Wang J. Org. Lett. 2023; 25: 3823
2h Zhu X, Wu H, Wang Y, Huang G, Wang F, Li X. Chem. Sci. 2023; 14: 8564
2i Zhu X, Mi R, Yin J, Wang F, Li X. Chem. Sci. 2023; 14: 7999
2j Mi R, Ding Z, Yu S, Crabtree RH, Li X. J. Am. Chem. Soc. 2023; 145: 8150
2k Zhu M, Zhao Y, Li X, Liu B. Org. Lett. 2023; 25: 1839
2l Wang P, Wu H, Zhang X.-P, Huang G, Crabtree RH, Li X. J. Am. Chem. Soc. 2023; 145: 8417
2m Zheng D.-S, Zhang W.-W, Gu Q, You S.-L. ACS Catal. 2023; 13: 5127

3a Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
3b Wencel-Delord J, Colobert F. Chem. Eur. J. 2013; 19: 14010
3c Zheng C, You S.-L. RSC Adv. 2014; 4: 6173
3d Newton CG, Wang S.-G, Oliveira CC, Cramer N. Chem. Rev. 2017; 117: 8908
3e Saint-Denis TG, Zhu R.-Y, Chen G, Wu Q.-F, Yu J.-Q. Science 2018; 359: eaao4798
3f Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
3g Wozniak Ł, Cramer N. Trends Chem. 2019; 1: 471
3h Yoshino T, Satake S, Matsunaga S. Chem. Eur. J. 2020; 26: 7346
3i Zhang Q, Shi B.-F. Acc. Chem. Res. 2021; 54: 2750
3j Zhan B.-B, Jin L, Shi B.-F. Trends Chem. 2022; 4: 220
3k McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
3l Gutekunsta WR, Baran PS. Chem. Soc. Rev. 2011; 40: 1976
3m Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
3n Abrams DJ, Provencher PA, Sorensen EJ. Chem. Soc. Rev. 2018; 47: 8925
3o Lam NY. S, Wu K, Yu J.-Q. Angew. Chem. Int. Ed. 2021; 60: 15767
3p Mas-Roselló J, Herraiz AG, Audic B, Laverny A, Cramer N. Angew. Chem. Int. Ed. 2021; 60: 13198
3q Liang H, Wang J. Chem. Eur. J. 2023; 29: e202202461
3r Liao G, Zhang T, Lin Z.-K, Shi B.-F. Angew. Chem. Int. Ed. 2020; 59: 19773
3s Yoshino T, Matsunaga S. ACS Catal. 2021; 11: 6455
3t Ye B, Cramer N. Acc. Chem. Res. 2015; 48: 1308
3u Shaaban S, Davies C, Waldmann H. Eur. J. Org. Chem. 2020; 6512
3v Achar T, Maiti KS, Jana S, Maiti D. ACS Catal. 2020; 10: 13748
3w Wang Q, Liu C.-X, Gu Q, You S.-L. Sci. Bull. 2021; 66: 210
3x Pan C, Yin S.-Y, Gua Q, You S.-L. Org. Biomol. Chem. 2021; 19: 7264
3y Yue Q, Liu B, Liao G, Shi B.-F. ACS Catal. 2022; 12: 9359
3z Yoshino T. Bull. Chem. Soc. Jpn. 2022; 95: 1280
3aa Qian P.-F, Li J.-Y, Zhou T, Shi B.-F. Synthesis 2022; 54: 4784
3ab Ye B, Cramer N. Science 2012; 338: 504
3ac Hyster TK, Knörr L, Ward TR, Rovis T. Science 2012; 338: 500
3ad Hassan IS, Ta AN, Danneman MW, Semakul N, Burns M, Basch CH, Dippon VN, McNaughton BR, Rovis T. J. Am. Chem. Soc. 2019; 141: 4815

4a Trifonova EA, Ankudinov NM, Mikhaylov AA, Chusov DA, Nelyubina YV, Perekalin DS. Angew. Chem. Int. Ed. 2018; 57: 7714
4b Kolos AV, Nelyubina YV, Sundararaju B, Perekalin DS. Organometallics 2021; 40: 3712
4c Jia Z.-J, Merten C, Gontla R, Daniliuc CG, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2017; 56: 2429
4d Audic B, Wodrich MD, Cramer N. Chem. Sci. 2019; 10: 781
4e Potter TJ, Kamber DN, Mercado DN, Ellman JA. ACS Catal. 2017; 7: 150
4f Yan X, Zhao P, Liang H, Xie H, Jiang J, Gou S, Wang J. Org. Lett. 2020; 22: 3219
4g Li G, Yan X, Jiang J, Liang H, Zhou C, Wang J. Angew. Chem. Int. Ed. 2020; 59: 22436
4h Liang H, Vasamsetty L, Li T, Jiang J, Pang X, Wang J. Chem. Eur. J. 2020; 26: 14546
4i Ye B, Cramer N. J. Am. Chem. Soc. 2013; 135: 636
4j Ye B, Donets PA, Cramer N. Angew. Chem. Int. Ed. 2014; 53: 507

5a Ye B, Cramer N. Synlett 2015; 26: 1490
5b Chen W, Li J, Xie H, Wang J. Org. Lett. 2020; 22: 3586
5c Zheng G, Zhou Z, Zhu G, Zhai S, Xu H, Duan X, Yi W, Li X. Angew. Chem. Int. Ed. 2020; 59: 2890
5d Mao R, Zhao Y, Zhu X, Wang F, Deng W.-Q, Li X. Org. Lett. 2021; 23: 7038
5e Duchemin C, Cramer N. Chem. Sci. 2019; 10: 2773
5f Duchemin C, Cramer N. Angew. Chem. Int. Ed. 2020; 59: 14129

6a Wu L, Xu H, Gao H, Li L, Chen W, Zhou Z, Yi W. ACS Catal. 2021; 11: 2279
6b Wu L, Li L, Zhang H, Gao H, Zhou Z, Yi W. Org. Lett. 2021; 23: 3844
6c Wei Y, Xu H, Chen F, Gao H, Huang Y, Yi W, Zhou Z. New J. Chem. 2022; 46: 5705
6d Wu M, Gao H, Xu H, Yi W, Zhou Z. Chin. Chem. Lett. 2022; 33: 842
6e Maity S, Potter TJ, Ellman JA. Nat. Catal. 2019; 2: 756
6f Mi R, Zhang X, Wang J, Chen H, Lan Y, Wang F, Li X. ACS Catal. 2021; 11: 6692
6g Brandes DS, Sirvent A, Mercado BQ, Ellman JA. Org. Lett. 2021; 23: 2836
6h Wang S.-G, Cramer N. Angew. Chem. Int. Ed. 2019; 58: 2514
6i Yang X, Zheng G, Li X. Angew. Chem. Int. Ed. 2019; 58: 322
6j Mi R, Zheng G, Qi Z, Li X. Angew. Chem. Int. Ed. 2019; 58: 17666

7a Ye B, Cramer N. Angew. Chem. Int. Ed. 2014; 53: 7896
7b Chen X, Yang S, Li H, Wang B, Song G. ACS Catal. 2017; 7: 2392
7c Liu B, Xie P, Zhao J, Wang J, Wang M, Jiang Y, Chang J, Li X. Angew. Chem. Int. Ed. 2021; 60: 8396
7d Li T, Zhou C, Yan X, Wang J. Angew. Chem. Int. Ed. 2018; 57: 4048
7e Wang S.-G, Liu Y, Cramer N. Angew. Chem. Int. Ed. 2019; 58: 18136
7f Wang S.-G, Cramer N. ACS Catal. 2020; 10: 8231
7g Cui W.-J, Wu Z.-J, Gu Q, You S.-L. J. Am. Chem. Soc. 2020; 142: 7379

8a Kong L, Han X, Liu S, Zou Y, Lan Y, Li X. Angew. Chem. Int. Ed. 2020; 59: 7188
8b Sun L, Liu B, Wang F, Deng W.-Q, Zhao Y, Chang J, Kong L, Li X. Chem. Commun. 2021; 57: 8268
8c Zheng J, Wang S.-B, Zheng C, You S.-L. J. Am. Chem. Soc. 2015; 137: 4880
8d Zheng C, Zheng J, You S.-L. ACS Catal. 2016; 6: 262
8e Chidipudi SR, Burns DJ, Khan I, Lam HW. Angew. Chem. Int. Ed. 2015; 54: 13975
8f Zheng J, Wang S.-B, Zheng C, You S.-L. Angew. Chem. Int. Ed. 2017; 56: 4540
8g Pham MV, Cramer N. Chem. Eur. J. 2016; 22: 2270
8h Li H, Gontla R, Flegel J, Merten C, Ziegler S, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2019; 58: 307
8i Huang Y.-Q, Wu Z.-J, Zhu L, Gu Q, Lu X, You S.-L, Mei T.-S. CCS Chem. 2022; 4: 3181
8j Wei W, Scheremetjew A, Ackermann L. Chem. Sci. 2022; 13: 2783

9a Shan G, Flegel J, Li H, Merten C, Ziegler S, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2018; 57: 14250
9b Tian M, Bai D, Zheng G, Chang J, Li X. J. Am. Chem. Soc. 2019; 141: 9527
9c Wang F, Qi Z, Zhao Y, Zhai S, Zheng G, Mi R, Huang Z, Zhu X, He X, Li X. Angew. Chem. Int. Ed. 2020; 59: 13288
9d Wang F, Jing J, Zhao Y, Zhu X, Zhang X.-P, Zhao L, Hu P, Deng W.-Q, Li X. Angew. Chem. Int. Ed. 2021; 60: 16628
9e Mi R, Chen H, Zhou X, Li N, Ji D, Wang F, Lan Y, Li X. Angew. Chem. Int. Ed. 2022; 61: e202111860
9f Li H, Yan X, Zhang J, Guo W, Jiang J, Wang J. Angew. Chem. Int. Ed. 2019; 58: 6732
9g Yan Y, Jiang J, Wang J. Angew. Chem. Int. Ed. 2022; 61: e202201522

10a Pan C, Yin S.-Y, Wang S.-B, Gu Q, You S.-L. Angew. Chem. Int. Ed. 2021; 60: 15510
10b Shaaban S, Merten C, Waldmann H. Chem. Eur. J. 2022; 28: e202103365
10c Zheng J, You S.-L. Angew. Chem. Int. Ed. 2014; 53: 13244
10d Zheng J, Cui W.-J, Zheng C, You S.-L. J. Am. Chem. Soc. 2016; 138: 5242
10e Wang Q, Zhang W.-W, Zheng C, Gu Q, You S.-L. J. Am. Chem. Soc. 2021; 143: 114
10f Zou Y, Wang P, Kong L, Li X. Org. Lett. 2022; 24: 3189

11a Sun Y, Cramer N. Angew. Chem. Int. Ed. 2017; 56: 364
11b Sun Y, Cramer N. Chem. Sci. 2018; 9: 2981
11c Sun Y, Cramer N. Angew. Chem. Int. Ed. 2018; 57: 15539
11d Brauns M, Cramer N. Angew. Chem. Int. Ed. 2019; 58: 8902
11e Hu P, Kong L, Wang F, Zhu X, Li X. Angew. Chem. Int. Ed. 2021; 60: 20424
11f Shen B, Wan B, Li X. Angew. Chem. Int. Ed. 2018; 57: 15534

12a Wang J, Chen H, Kong L, Wang F, Lan Y, Li X. ACS Catal. 2021; 11: 9151
12b Wang S.-B, Zheng J, You S.-L. Organometallics 2016; 35: 1420
12c Wang S.-B, Gu Q, You S.-L. Organometallics 2017; 36: 4359
12d Wang Q, Nie Y.-H, Liu C.-X, Zhang W.-W, Wu Z.-J, Gu Q, Zheng C, You S.-L. ACS Catal. 2022; 12: 3083
12e Wang Q, Zhang W.-W, Song H, Wang J, Zheng C, Gu Q, You S.-L. J. Am. Chem. Soc. 2020; 142: 15678
12f Zhang W.-W, Liu C.-X, Yang P, Zhang S.-Z, Gu Q, You S.-L. Org. Lett. 2022; 24: 564
12g Kurihara T, Kojima M, Yoshino T, Matsunaga S. J. Am. Chem. Soc. 2022; 144: 7058

13a Lin L, Fukagawa S, Sekine D, Tomita E, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed. 2018; 57: 12048
13b Fukagawa S, Kojima M, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed. 2019; 58: 18154
13c Huang L.-T, Fukagawa S, Kojima M, Yoshino T, Matsunaga S. Org. Lett. 2020; 22: 8256
13d Kato Y, Lin L, Kojima M, Yoshino T, Matsunaga S. ACS Catal. 2021; 11: 4271
13e Satake S, Kurihara T, Nishikawa K, Mochizuki T, Hatano M, Ishihara K, Yoshino T, Matsunaga S. Nat. Catal. 2018; 1: 585
13f Hirose J, Wakikawa T, Satake S, Kojima M, Hatano M, Ishihara K, Yoshino T, Matsunaga S. ACS Catal. 2021; 11: 15187
13g Li G, Jiang J, Xie H, Wang J. Chem. Eur. J. 2019; 25: 4688

14a Jang Y.-S, Dieckmann M, Cramer N. Angew. Chem. Int. Ed. 2017; 56: 15088
14b Jang Y.-S, Wozniak Ł, Pedroni J, Cramer N. Angew. Chem. Int. Ed. 2018; 57: 12901
14c Wozniak Ł, Cramer N. Angew. Chem. Int. Ed. 2021; 60: 18532
14d Zimbron JM, Heinisch T, Schmid M, Hamels D, Nogueira ES, Schirmer T, Ward TR. J. Am. Chem. Soc. 2013; 135: 5384

15a Gwon D, Park S, Chang S. Tetrahedron 2015; 71: 4504
15b Zhang C.-W, Hu X.-Q, Dai Y.-H, Yin P, Wang C, Duan W.-L. ACS Catal. 2022; 12: 193
15c Liu W, Yang W, Zhu J, Guo Y, Wang N, Ke J, Yu P, He C. ACS Catal. 2020; 10: 7207
15d Liu L, Song H, Liu Y.-H, Wu L.-S, Shi B.-F. ACS Catal. 2020; 10: 7117
15e Li J.-Y, Xie P.-P, Zhou T, Qian P.-F, Zhou Y.-B, Li H.-C, Hong X, Shi B.-F. ACS Catal. 2022; 12: 9083

16a Ozols K, Jang Y.-S, Cramer N. J. Am. Chem. Soc. 2019; 141: 5675
16b Ozols K, Onodera S, Woźniak Ł, Cramer N. Angew. Chem. Int. Ed. 2021; 60: 655
16c Herraiz AG, Cramer N. ACS Catal. 2021; 11: 11938
16d Pesciaioli F, Dhawa U, Oliveira JC. A, Yin R, John M, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 15425

17a Fukagawa S, Kato Y, Tanaka R, Kojima M, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed. 2019; 58: 1153
17b Sekine D, Ikeda K, Fukagawa S, Kojima M, Yoshino T, Matsunaga S. Organometallics 2019; 38: 3921
17c Liu Y.-H, Li P.-X, Yao Q.-J, Zhang Z.-Z, Huang D.-Y, Le MD, Song H, Liu L, Shi B.-F. Org. Lett. 2019; 21: 1895
17d Liu Y.-H, Xie P.-P, Liu L, Fan J, Zhang Z.-Z, Hong X, Shi B.-F. J. Am. Chem. Soc. 2021; 143: 19112
17e Hirata Y, Sekine D, Kato Y, Lin L, Kojima M, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed. 2022; 61: e202205341
17f Zhou Y.-B, Zhou T, Qian P.-F, Li J.-Y, Shi B.-F. ACS Catal. 2022; 12: 9806

18a Liang H, Guo W, Li J, Jiang J, Wang J. Angew. Chem. Int. Ed. 2022; 61: e202204926
18b Li Z.-Y, Lakmal HH. C, Qian X, Zhu Z, Donnadieu B, McClain SJ, Xu X, Cui X. J. Am. Chem. Soc. 2019; 141: 15730
18c Li G, Liu Q, Vasamsetty L, Guo W, Wang J. Angew. Chem. Int. Ed. 2020; 59: 3475
18d Dethe DH, Beeralingappa NC, Siddiqui SA, Chavan PN. J. Org. Chem. 2022; 87: 4617
18e Zhou T, Qian P-F, Li J.-Y, Zhou Y.-B, Li H.-C, Chen H.-Y, Shi B.-F. J. Am. Chem. Soc. 2021; 143: 6810
18f Huang L.-T, Hirata Y, Kato Y, Lin L, Kojima M, Yoshino T, Matsunaga S. Synthesis 2022; 54: 4703
18g Qian P.-F, Zhou T, Li J.-Y, Zhou Y.-B, Shi B.-F. ACS Catal. 2022; 12: 13876
18h Dhawa U, Connon R, Oliveira JC. A, Steinbock R, Ackermann L. Org. Lett. 2021; 23: 2760
18i Li Y, Liou Y.-C, Oliveira JC. A, Ackermann L. Angew. Chem. Int. Ed. 2022; 61: e202212595