Ni- and Pd-Catalyzed Enantioselective 1,2-Dicarbofunctionalization of Alkenes

Taeho Kang; Omar Apolinar; Keary M. Engle

doi:10.1055/a-2108-9549

Synthesis, Table of Contents

Synthesis 2024; 56(01): 1-15
DOI: 10.1055/a-2108-9549

review

Ni- and Pd-Catalyzed Enantioselective 1,2-Dicarbofunctionalization of Alkenes

Taeho Kang‡

,

Omar Apolinar‡

,

Keary M. Engle ∗

Abstract

All articles of this category

Abstract

Catalytic enantioselective 1,2-dicarbofunctionalization (1,2-DCF) of alkenes is a powerful transformation of growing importance in organic synthesis for constructing chiral building blocks, bioactive molecules, and agrochemicals. Both in a two- and three-component context, this family of reactions generates densely functionalized, structurally complex products in a single step. Across several distinct mechanistic pathways at play in these transformations with nickel or palladium catalysts, stereocontrol can be obtained through tailored chiral ligands. In this Review we discuss the various strategies, mechanisms, and catalysts that have been applied to achieve enantioinduction in alkene 1,2-DCF.

1 Introduction

2 Two-Component Enantioselective 1,2-DCF via Migratory Insertion

3 Two-Component Enantioselective 1,2-DCF via Radical Capture

4 Three-Component Enantioselective 1,2-DCF via Radical Capture

5 Three-Component Enantioselective 1,2-DCF via Migratory Insertion

6 Miscellaneous Mechanisms

7 Conclusion

Key words

alkenes - cross-coupling - dicarbofunctionalization - enantioselectivity - nickel - palladium

Full Text

References

References

1a Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
1b Lovering F. Med. Chem. Commun. 2013; 4: 515
1c Li J, Eastgate MD. Org. Biomol. Chem. 2015; 13: 7164
1d Eastgate MD, Schmidt MA, Fandrick KR. Nat. Rev. Chem. 2017; 1: 0016
1e Caille S, Cui S, Faul MM, Mennen SM, Tedrow JS, Walker SD. J. Org. Chem. 2019; 84: 4583
1f Beaver MG, Caille S, Farrell RP, Rötheli AR, Smith AG, Tedrow JS, Thiel OR. Synlett 2021; 32: 457

For representative reviews on transition-metal-catalyzed C(sp^2/3)–C(sp³) cross-couplings see:

2a Hayashi T, Yamasaki K. Chem. Rev. 2003; 103: 2829
2b Trost BM, Van Vranken DL. Chem. Rev. 1996; 96: 395
2c Kranthikumar R. Organometallics 2022; 41: 667
2d Cherney AH, Kadunce NT, Reisman SE. Chem. Rev. 2015; 115: 9587

For reviews on nonstereoselective Pd- and Ni-catalyzed 1,2-dicarbofunctionalization of alkenes:

3a Derosa J, Tran VT, van der Puyl VA, Engle KM. Aldrichimica Acta 2018; 51: 21
3b Giri R, KC SC. J. Org. Chem. 2018; 83: 3013
3c Tu H.-Y, Zhu S, Qing F.-L, Chu L. Synthesis 2020; 52: 1346
3d Badir SO, Molander GA. Chem 2020; 6: 1327
3e Derosa J, Apolinar O, Kang T, Tran VT, Engle KM. Chem. Sci. 2020; 11: 4287
3f Qi X, Diao T. ACS Catal. 2020; 10: 8542
3g Lee BC, Liu C.-F, Lin LQ. H, Yap KZ, Song N, Ko CH. M, Chan PH, Koh MJ. Chem. Soc. Rev. 2023; 52: 2946

4a Leatherman MD, Svejda SA, Johnson LK, Brookhart M. J. Am. Chem. Soc. 2003; 125: 3068
4b Xu H, White PB, Hu C, Diao T. Angew. Chem. Int. Ed. 2017; 56: 1535
4c Xu H, Hu CT, Wang X, Diao T. Organometallics 2017; 36: 4099

For a recent review on enantioselective radical-based Cu-catalyzed 1,2-DCF of alkenes see:

5a Li Z.-L, Fang G.-C, Gu Q.-S, Liu X.-Y. Chem. Soc. Rev. 2020; 49: 32

For closed-shell enantioselective Cu-catalyzed 1,2-DCF of alkenes see:

5b You W, Brown MK. J. Am. Chem. Soc. 2015; 137: 14578

For enantioselective Rh-catalyzed 1,2-DCF of alkenes see:

5c Shintani R, Okamoto K, Otomaru Y, Ueyama K, Hayashi T. J. Am. Chem. Soc. 2005; 127: 54
5d Miura T, Sasaki T, Nakazawa H, Murakami M. J. Am. Chem. Soc. 2005; 127: 1390
5e Xu T, Ko HM, Savage NA, Dong G. J. Am. Chem. Soc. 2012; 134: 20005

For enantioselective Co-catalyzed 1,2-DCF of alkenes see:

5f Herraiz AG, Cramer N. ACS Catal. 2021; 11: 11938

6a Catellani M, Chiusoli GP. Tetrahedron Lett. 1982; 23: 4517
6b Catellani M, Chiusoli GP, Giroldini W, Salerno G. J. Organomet. Chem. 1980; 199: C21
6c Catellani M, Chiusoli GP. J. Organomet. Chem. 1982; 233: C21
6d Catellani M, Chiusoli GP, Sgarabotto P. J. Organomet. Chem. 1982; 240: 311

7a Sato Y, Sodeoka M, Shibasaki M. J. Org. Chem. 1989; 54: 4738
7b Carpenter NE, Kucera DJ, Overman LE. J. Org. Chem. 1989; 54: 5846
7c Dounay AB, Overman LE. Chem. Rev. 2003; 103: 2945

8 Ohshima T, Kagechika K, Adachi M, Sodeoka M, Shibasaki M. J. Am. Chem. Soc. 1996; 118: 7108

9a Diaz P, Gendre F, Stella L, Charpentier B. Tetrahedron 1998; 54: 4579
9b Yue G, Lei K, Hirao H, Zhou J. Angew. Chem. Int. Ed. 2015; 54: 6531

10a Pinto A, Jia Y, Neuville L, Zhu J. Chem. Eur. J. 2007; 13: 961
10b Yasui Y, Kamisaki H, Takemoto Y. Org. Lett. 2008; 10: 3303
10c Watson MP, Jacobsen EN. J. Am. Chem. Soc. 2008; 130: 12594
10d Nakao Y, Ebata S, Yada A, Hiyama T, Ikawa M, Ogoshi S. J. Am. Chem. Soc. 2008; 130: 12874

11 Cong H, Fu GC. J. Am. Chem. Soc. 2014; 136: 3788
12 Kong W, Wang Q, Zhu J. J. Am. Chem. Soc. 2015; 137: 16028
13 Kong W, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2016; 55: 9714
14 Carmona RC, Köster OD, Correia CR. D. Angew. Chem. Int. Ed. 2018; 57: 12067
15 Ma T, Chen Y, Li Y, Ping Y, Kong W. ACS Catal. 2019; 9: 9127

16a Zhang Z.-M, Xu B, Wu L, Wu Y, Qian Y, Zhou L, Liu Y, Zhang J. Angew. Chem. Int. Ed. 2019; 58: 14653
16b Ju B, Chen S, Kong W. Chem. Commun. 2019; 55: 14311
16c Chen Q, Li S, Xie X, Guo H, Yang J, Zhang J. Org. Lett. 2021; 23: 4099
16d Ma Z, Sun L, Zhou JS. Sci. China: Chem. 2023; 66: 1701

17a Zhou L, Li S, Xu B, Ji D, Wu L, Liu Y, Zhang Z.-M, Zhang J. Angew. Chem. Int. Ed. 2020; 59: 2769
17b Liu R.-R, Wang Y.-G, Li Y.-L, Huang B.-B, Liang R.-X, Jia Y.-X. Angew. Chem. Int. Ed. 2017; 56: 7475
17c Wu Y, Xu B, Zhao G, Pan Z, Zhang Z.-M, Zhang J. Chin. J. Chem. 2021; 39: 3255

18a Liu L, Cheng F, Meng C, Zhang A.-A, Zhang M, Xu K, Ishida N, Murakami M. ACS Catal. 2021; 11: 8942
18b Cao K, Zhang Z.-M, Zhang J, Chen F. Org. Lett. 2021; 23: 9520

19a Ping Y, Li Y, Zhu J, Kong W. Angew. Chem. Int. Ed. 2019; 58: 1562
19b Xu B, Ji D, Wu L, Zhou L, Liu Y, Zhang Z.-M, Zhang J. Chem 2022; 8: 836

20 Diccianni J, Lin Q, Diao T. Acc. Chem. Res. 2020; 53: 906
21 Wang K, Ding Z, Zhou Z, Kong W. J. Am. Chem. Soc. 2018; 140: 12364
22 Jin Y, Wang C. Angew. Chem. Int. Ed. 2019; 58: 6722
23 Tian Z.-X, Qiao J.-B, Xu G.-L, Pang X, Qi L, Ma W.-Y, Zhao Z.-Z, Duan J, Du Y.-F, Su P, Liu X.-Y, Shu X.-Z. J. Am. Chem. Soc. 2019; 141: 7637
24 Li Y, Ding Z, Lei A, Kong W. Org. Chem. Front. 2019; 6: 3305
25 Jin Y, Yang H, Wang C. Org. Lett. 2020; 22: 2724
26 Williams MT, Morrill LC, Browne DC. Adv. Synth. Catal. 2023; 365: 1477
27 Fan P, Lan Y, Zhang C, Wang C. J. Am. Chem. Soc. 2020; 142: 2180

28a Wu X, Qu J, Chen Y. J. Am. Chem. Soc. 2020; 142: 15654
28b Wu X, Luan B, Zhao W, He F, Wu X.-Y, Qu J, Chen Y. Angew. Chem. Int. Ed. 2022; 61: e202111598

29 Li Y, Zhang F.-P, Wang R.-H, Qi S.-L, Luan Y.-X, Ye M. J. Am. Chem. Soc. 2020; 142: 19844
30 Lan Y, Wang C. Commun. Chem. 2020; 3: 45
31 Chierchia M, Xu P, Lovinger GJ, Morken JP. Angew. Chem. Int. Ed. 2019; 58: 14245
32 Gu J.-W, Min Q.-Q, Yu L.-C, Zhang X. Angew. Chem. Int. Ed. 2016; 55: 12270

33a Anthony D, Lin Q, Baudet J, Diao T. Angew. Chem. Int. Ed. 2019; 58: 3198
33b Lin Q, Spielvogel EH, Diao T. Chem 2023; 9: 1295

34 Tu H.-Y, Wang F, Huo L, Li Y, Zhu S, Zhao X, Li H, Qing F.-L, Chu L. J. Am. Chem. Soc. 2020; 142: 9604

35a Wei X, Shu W, García-Domínguez A, Merino E, Nevado C. J. Am. Chem. Soc. 2020; 142: 13515
35b García-Domínguez A, Li Z, Nevado C. J. Am. Chem. Soc. 2017; 139: 6835

36 Li Y.-Z, Rao N, An L, Wan X.-L, Zhang Y, Zhang X. Nat. Commun. 2022; 13: 5539

37a Li X, Yuan M, Chen F, Huang Z, Qing F.-L, Gutierrez O, Chu L. Chem 2023; 9: 154
37b Guo L, Yuan M, Zhang Y, Wang F, Zhu S, Gutierrez O, Chu L. J. Am. Chem. Soc. 2020; 142: 20390

38a Kang T, Kim N, Cheng PT, Zhang H, Foo K, Engle KM. J. Am. Chem. Soc. 2021; 143: 13962
38b Kang T, González JM, Li Z.-Q, Foo K, Cheng PT. W, Engle KM. ACS Catal. 2022; 12: 3890
38c Li Z.-Q, Cao Y, Kang T, Engle KM. J. Am. Chem. Soc. 2022; 144: 7189

39 Stokes BJ, Liao L, de Andrade AM, Wang Q, Sigman MS. Org. Lett. 2014; 16: 4666
40 Wu X, Lin H.-C, Li M.-L, Li L.-L, Han Z.-Y, Gong L.-Z. J. Am. Chem. Soc. 2015; 137: 13476
41 Zhang Y, Chen G, Zhao D. Chem. Sci. 2019; 10: 7952
42 Xi Y, Huang W, Wang C, Ding H, Xia T, Wu L, Fang K, Qu J, Chen Y. J. Am. Chem. Soc. 2022; 144: 8389
43 Apolinar O, Kang T, Alturaifi TM, Bedekar PG, Rubel CZ, Derosa J, Sanchez BB, Wong QN, Sturgell EJ, Chen JS, Wisniewski SR, Liu P, Engle KM. J. Am. Chem. Soc. 2022; 144: 19337
44 Liu C.-F, Wang Z.-C, Luo X, Lu J, Ko CH. M, Shi S.-L, Koh MJ. Nat. Catal. 2022; 5: 934
45 Dong Z, Tang Q, Xu C, Chen L, Ji H, Zhou S, Song L, Chen L.-A. Angew. Chem. Int. Ed. 2023; 62: e202218286
46 Zhang L, Lovinger GJ, Edelstein EK, Szymaniak AA, Chierchia MP, Morken JP. Science 2016; 351: 70
47 Teng S, Chi YR, Zhou JS. Angew. Chem. Int. Ed. 2021; 60: 4491