Earth-Abundant Transition Metal Catalyzed Asymmetric Hydrogenation of Minimally Functionalized Alkenes

Peng Lu; Zhan Lu

doi:10.1055/a-2000-8183

Synthesis, Table of Contents

Synthesis 2023; 55(07): 1042-1052
DOI: 10.1055/a-2000-8183

short review

Earth-Abundant Transition Metal Catalyzed Asymmetric Hydrogenation of Minimally Functionalized Alkenes

Peng Lu

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

,

Zhan Lu ∗

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

^bCollege of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. of China

› Author Affiliations

Abstract

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Abstract

Transition-metal-catalyzed asymmetric hydrogenation (AH) is a growing field and a fundamental tool for the construction of chiral compounds. The use of earth-abundant transition metals in AH reactions remains generally limited but has received increased attention in recent years due to cost, sustainability, and environmental concerns. Here, we will summarize progress in first row transition metal catalyzed AH of minimally functionalized alkenes, including scope, mechanism, and challenges in this field.

1 Introduction

2 Ti-Catalyzed AH of Minimally Functionalized Alkenes

3 Zr-Catalyzed AH of Minimally Functionalized Alkenes

4 Co-Catalyzed AH of Minimally Functionalized Alkenes

5 Fe-Catalyzed AH of Minimally Functionalized Alkenes

6 Summary and Outlook

Key words

asymmetric hydrogenation - minimally functionalized alkenes - earth-abundant transition metals - catalysis - ligand design

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References

References

1a Johnson NB, Lennon IC, Moran PH, Ramsden JA. Acc. Chem. Res. 2007; 40: 1291
1b Shultz CS, Krska SW. Acc. Chem. Res. 2007; 40: 1320
1c Etayoa P, Vidal-Ferran A. Chem. Soc. Rev. 2013; 42: 728

2 Knowles WS, Sabacky MJ. Chem. Commun. 1968; 1445
3 Horner L, Siegel H, Büthe H. Angew. Chem., Int. Ed. Engl. 1968; 7: 941
4 Dang TP, Kagan HB. J. Chem. Soc. D. 1971; 481
5 Vineyard BD, Knowles WS, Sabacky MJ, Bachman GL, Weinkauff OJ. J. Am. Chem. Soc. 1977; 99: 5946

6a Noyori R. Chem. Soc. Rev. 1989; 18: 187
6b Noyori R, Takaya H. Acc. Chem. Res. 1990; 23: 345
6c Noyori R. Science 1990; 248: 1194

7a Noyori R. Angew. Chem. Int. Ed. 2002; 41: 2008
7b Knowles WS. Angew. Chem. Int. Ed. 2002; 41: 1998

8a Tang W, Zhang X. Chem. Rev. 2003; 103: 3029
8b Zhao D, Candish L, Paul D, Glorius F. ACS Catal. 2016; 6: 5978
8c Zhang Z, Butt NA, Zhang W. Chem. Rev. 2016; 116: 14769
8d Zhou Y.-G. Acc. Chem. Res. 2007; 40: 1357
8e Zhu S.-F, Zhou Q.-L. Acc. Chem. Res. 2017; 50: 988
8f Charvillat T, Bernardelli P, Daumas M, Pannecoucke X, Ferey V, Besset T. Chem. Soc. Rev. 2021; 50: 8178

9a Crabtree RH, Felkin H, Morris GE. J. Organomet. Chem. 1977; 141: 205
9b Crabtree RH, Gautier A, Giordano G, Khan T. J. Organomet. Chem. 1977; 141: 113

10a Schnider P, Koch G, Prétôt R, Wang G, Bohnen FM, Krüger C, Pfaltz A. Chem. Eur. J. 1997; 3: 887
10b Lightfoot A, Schnider P, Pfaltz A. Angew. Chem. Int. Ed. 1998; 37: 2897

11 Helmchen G, Pfaltz A. Acc. Chem. Res. 2000; 33: 336

12a Roseblade SJ, Pfaltz A. Acc. Chem. Res. 2007; 40: 1402
12b Cui X, Burgess K. Chem. Rev. 2005; 105: 3272
12c Verendel JJ, Pamies O, Diéguez M, Andersson PG. Chem. Rev. 2014; 114: 2130
12d Biosca M, Magre M, Pamies O, Diéguez M. ACS Catal. 2018; 8: 10316
12e Bunlaksananusorn T, Polborn K, Knochel P. Angew. Chem. Int. Ed. 2003; 42: 3941
12f Bell S, Wüstenberg B, Kaiser S, Menges F, Netscher T, Pfaltz A. Science 2006; 311: 642
12g Biosca M, Salomo E, Cruz-Sanchez P, Riera A, Verdaguer X, Pamies O, Diéguez M. Org. Lett. 2019; 21: 807
12h Wassenaar J, Detz RJ, Boer SY, Lutz M, Maarseveen JH, Hiemstra H, Reek JN. H. J. Org. Chem. 2015; 80: 3634

13 Powell MT, Hou D.-R, Perry MC, Cui X, Burgess K. J. Am. Chem. Soc. 2001; 123: 8878
14 Drury WJ, Zimmermann N, Keenan M, Hayashi M, Kaiser S, Goddard R, Pfaltz A. Angew. Chem. Int. Ed. 2004; 43: 70
15 Schumacher A, Bernasconi M, Pfaltz A. Angew. Chem. Int. Ed. 2013; 52: 7422
16 Liu Q.-B, Zhou Y.-G. Tetrahedron Lett. 2007; 48: 2101

17a Källström K, Hedberg C, Brandt P, Bayer A, Andersson PG. J. Am. Chem. Soc. 2004; 126: 14308
17b Hedberg C, Källström K, Brandt P, Hansen LK, Andersson PG. J. Am. Chem. Soc. 2006; 128: 2995

18a Mazuela J, Norrby P.-O, Andersson PG, Pàmies O, Diéguez M. J. Am. Chem. Soc. 2011; 133: 13634
18b Mazuela J, Pàmies O, Diéguez M. ChemCatChem 2013; 5: 2410

19 Busacca CA, Qu B, Grět N, Fandrick KR, Saha AK, Marsini M, Reeves D, Haddad N, Eriksson M, Wu J.-P, Grinberg N, Lee H, Li Z, Lu B, Chen D, Hong Y, Ma S, Senanayake CH. Adv. Synth. Catal. 2013; 355: 1455

20a Chatterjee I, Qu Z.-W, Grimme S, Oestreich M. Angew. Chem. Int. Ed. 2015; 54: 12158
20b Keess S, Oestreich M. Chem. Sci. 2017; 8: 4688
20c Wang D, Astruc D. Chem. Rev. 2015; 115: 6621

21a Pálvölgyi ÁM, Scharinger F, Schnürch M, Bica-Schröder K. Eur. J. Org. Chem. 2021; 5367
21b Noyori R, Hashiguchi S. Acc. Chem. Res. 1997; 30: 97
21c Li Y.-Y, Yu S.-L, Shen W.-Y, Gao J.-X. Acc. Chem. Res. 2015; 48: 2587
21d Zassinovich G, Mestroni G, Gladiali S. Chem. Rev. 1992; 92: 1051
21e Palmer MJ, Wills M. Tetrahedron: Asymmetry 1999; 10: 2045
21f Gladiali S, Alberico E. Chem. Soc. Rev. 2006; 35: 226
21g Yang JW, Fonseca MT. H, List B. Angew. Chem. Int. Ed. 2004; 43: 6660
21h Xu H, Yang P, Chuanprasit P, Hirao H, Zhou J. Angew. Chem. Int. Ed. 2015; 54: 5112

22a Wang Y, Huang Z, Liu G, Huang Z. Acc. Chem. Res. 2022; 55: 2148
22b Wang Z, Ai F, Wang Z, Zhao W, Zhu G, Lin Z, Sun J. J. Am. Chem. Soc. 2015; 137: 383

23 Margarita C, Andersson PG. J. Am. Chem. Soc. 2017; 139: 1346

24a Zhang Z, Butt NA, Zhou M, Liu D, Zhang W. Chin. J. Chem. 2018; 36: 443
24b Wen J, Wang F, Zhang X. Chem. Soc. Rev. 2021; 50: 3211
24c Ai W, Zhong R, Liu X, Liu Q. Chem. Rev. 2019; 119: 2876
24d Le Bailly BA. F, Thomas SP. RSC Adv. 2011; 1: 1435
24e Gieshoff TN, von Wangelin AJ. C=C Hydrogenations with Iron Group Metal Catalysts . In Non-Noble Metal Catalysis: Molecular Approaches and Reactions . Gebbink RJ. M. K, Moret M.-E. Wiley-VCH; Weinheim: 2018: 97
24f Teichert JF. Homogeneous Hydrogenation with Non-Precious Catalysts. Wiley-VCH; Weinheim: 2019

25a Marks TJ. Acc. Chem. Res. 1992; 25: 57
25b Kesti MR, Coates GW, Waymouth RM. J. Am. Chem. Soc. 1992; 114: 9679
25c Pino P, Cioni P, Wei J. J. Am. Chem. Soc. 1987; 109: 6189

26 Cesarotti E, Ugo R, Kagan HB. Angew. Chem., Int. Ed. Engl. 1979; 18: 779
27 Halterman RL, Vollhardt KP. C, Welker ME, Blaeser D, Boese R. J. Am. Chem. Soc. 1987; 109: 8105
28 Wild FR. W. P, Zsolnai L, Huttner G, Brintzinger HH. J. Organomet. Chem. 1982; 232: 233
29 Broene RD, Buchwald SL. J. Am. Chem. Soc. 1993; 115: 12569
30 Waymouth R, Pino P. J. Am. Chem. Soc. 1990; 112: 4911
31 Troutman MV, Appella DH, Buchwald SL. J. Am. Chem. Soc. 1999; 121: 4916
32 It’s Elemental: The Periodic Table of Elements, Jefferson Lab Resources, Thomas Jefferson National Accelerator Facility - Office of Science Education (accessed January 2, 2023): https://education.jlab.org/itselemental/
33 Ohgo Y, Takeuchi S, Natori Y, Yoshimura J. Bull. Chem. Soc. Jpn. 1981; 54: 2124
34 Yoshinaga K, Kito T, Oka H, Sakaki S, Ohkubo K. J. Catal. 1984; 87: 517
35 Leutenegger U, Madin A, Pfaltz A. Angew. Chem., Int. Ed. Engl. 1989; 28: 60
36 Corma A, Iglesias M, del Pino C, Sanchez F. J. Organomet. Chem. 1992; 431: 233

37a Friedfeld MR, Shevlin M, Hoyt JM, Krska SW, Tudge MT, Chirik PJ. Science 2013; 342: 1076
37b Friedfeld MR, Zhong H, Ruck RT, Shevlin M, Chirik PJ. Science 2018; 360: 888
37c Du X, Xiao Y, Yang Y, Duan Y.-N, Li F, Hu Q, Chung LW, Chen G.-Q, Zhang X. Angew. Chem. Int. Ed. 2021; 60: 11384
37d Du X, Xiao Y, Huang J.-M, Zhang Y, Duan Y.-N, Wang H, Shi C, Chen G.-Q, Zhang X. Nat. Commun. 2020; 11: 3239

38 Monfette S, Turner ZR, Semproni SP, Chirik PJ. J. Am. Chem. Soc. 2012; 134: 4561
39 Friedfeld MR, Shevlin M, Margulieux GW, Campeau L.-C, Chirik PJ. J. Am. Chem. Soc. 2016; 138: 3314
40 Hopmann KH. Organometallics 2013; 32: 6388
41 Chen J, Chen C, Ji C, Lu Z. Org. Lett. 2016; 18: 1594
42 Mazuela J, Pàmies O, Diéguez M. Eur. J. Inorg. Chem. 2013; 2139
43 Massaro L, Zheng J, Margarita C, Andersson PG. Chem. Soc. Rev. 2020; 49: 2504
44 Lu P, Wang H, Mao Y, Hong X, Lu Z. J. Am. Chem. Soc. 2022; 144: 17359
45 The DFT calculations of mechanism is being prepared for submission.
46 Gopalaiah K. Chem. Rev. 2013; 113: 3248
47 Frankel EN, Emken EA, Peters HM, Davison VL, Butterfield RO. J. Org. Chem. 1964; 29: 3292

48a Bart SC, Lobkovsky E, Chirik PJ. J. Am. Chem. Soc. 2004; 126: 13794
48b Chirik PJ. Acc. Chem. Res. 2015; 48: 1687
48c Guo N, Hu M.-Y, Feng Y, Zhu S.-F. Org. Chem. Front. 2015; 2: 692
48d Frank DJ, Guiet L, Käslin A, Murphy E, Thomas SP. RSC Adv. 2013; 3: 25698
48e Daida EJ, Peters JC. Inorg. Chem. 2004; 43: 7474
48f Sunada Y, Ogushi H, Yamamoto T, Uto S, Sawano M, Tahara A, Tanaka H, Shiota Y, Yoshizawa K, Nagashima H. J. Am. Chem. Soc. 2018; 140: 4119
48g Docherty JH, Peng J, Dominey AP, Thomas SP. Nat. Chem. 2017; 9: 595

49 Hoyt JM, Shevlin M, Margulieux GW, Krska SW, Tudge MT, Chirik PJ. Organometallics 2014; 33: 5781

50a Danopoulos AA, Wright JA, Motherwell WB. Chem. Commun. 2005; 784
50b Danopoulos AA, Pugh D, Smith H, Saßmannshausen J. Chem. Eur. J. 2009; 15: 5491

51 Viereck P, Rummelt SM, Soja NA, Pabst TP, Chirik PJ. Organometallics 2021; 40: 1053
52 Lu P, Ren X, Xu H, Lu D, Sun Y, Lu Z. J. Am. Chem. Soc. 2021; 143: 12433