C–H Functionalization of Arenes via NHC-Supported Ni/Al Bimetallic Catalysis

Binyang Jiang; Shi-Liang Shi

doi:10.1055/a-2114-5508

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(24): 4049-4061
DOI: 10.1055/a-2114-5508

short review

C–H Functionalization of Arenes via NHC-Supported Ni/Al Bimetallic Catalysis

Binyang Jiang

,

Shi-Liang Shi ∗

Abstract

Alle Artikel dieser Rubrik

Abstract

Despite the C–H functionalization of arenes offering an efficient synthetic route towards functionalized aromatic compounds with high atom- and step-economy, the low reactivity of the C–H bond makes this transformation rather challenging. Compared with mono-metal catalysis, the introduction of bimetallic catalysis would greatly enhance the reactivity and selectivity of this transformation. In this review, we highlight recent progress in the C–H functionalization of arenes via NHC-Ni/Al catalysis. The added aluminum as a co-catalyst would activate arene through Lewis acid-base interaction, and regioselectivity could be controlled through the synergism of NHC-Ni and Al. This strategy could be also applied in enantioselective C–H alkylation with well-designed chiral NHC ligands.

1 Introduction

2 C–H Addition to Alkynes via C–H Activation

3 C–H Alkylation via Ni/Al Bimetallic Catalysis

3.1 Racemic Hydroarylation with Alkenes

3.2 Asymmetric Hydroarylation with Alkenes

4 Conclusion and Outlook

Keywords

nickel catalysis - Lewis acid - C–H functionalization - NHC ligand - bimetallic catalysis - synthetic methodology

Volltext

Referenzen

References

1a Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; New York: 1998
1b Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6722

2a Khake SM, Chatani N. Trends Chem. 2019; 1: 524
2b Rogge T, Kaplaneris N, Chatani N, Kim J, Chang S, Punji B, Schafer LL, Musaev DG, Wencel-Delord J, Roberts CA, Sarpong R, Wilson ZE, Brimble MA, Johansson MJ, Ackermann L. Nat. Rev. Methods Primers 2021; 1: 43
2c Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
2d Dalton T, Faber T, Glorius F. ACS Cent. Sci. 2021; 7: 245
2e Mandal D, Roychowdhury S, Biswas JP, Maiti S, Maiti D. Chem. Soc. Rev. 2022; 51: 7358

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

4a Rousseau G, Breit B. Angew. Chem. Int. Ed. 2011; 50: 2450
4b Rouquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
4c Zhu R.-Y, Farmer ME, Chen Y.-Q, Yu J.-Q. Angew. Chem. Int. Ed. 2016; 55: 10578

5a Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
5b Haldar C, Emdadul Hoque M, Bisht R, Chattopadhyay B. Tetrahedron Lett. 2018; 59: 1269
5c Choi J, Goldman AS. Top. Organomet. Chem. 2011; 34: 139
5d Piou T, Rovis T. Acc. Chem. Res. 2018; 51: 170
5e Nareddy P, Jordan F, Szostak M. ACS Catal. 2017; 7: 5721

6a Xu W, Li M, Qiao L, Xie J. Chem. Commun. 2020; 56: 8524
6b Kim UB, Jung DJ, Jeon HJ, Rathwell K, Lee S. Chem. Rev. 2020; 120: 13382
6c Becica J, Dobereiner GE. Org. Biomol. Chem. 2019; 17: 2055

7 Wang Y.-X, Ye M. Sci. China: Chem. 2018; 61: 1004

8a Clement ND, Cavell KJ. Angew. Chem. Int. Ed. 2004; 43: 3845
8b Normand AT, Hawkes KJ, Clement ND, Cavell KJ, Yates BF. Organometallics 2007; 26: 5352

9a Nakao Y, Kanyiva KS, Oda S, Hiyama T. J. Am. Chem. Soc. 2006; 128: 8146
9b Kanyiva KS, Nakao Y, Hiyama T. Angew. Chem. Int. Ed. 2007; 46: 8872
9c Kanyiva KS, Nakao Y, Hiyama T. Heterocycles 2007; 72: 677
9d Nakao Y, Kashihara N, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2008; 130: 16170
9e Nakao Y. Chem. Rec. 2011; 11: 242

10a Huynh HV. Chem. Rev. 2018; 118: 9457
10b Nelson DJ, Nolan SP. Chem. Soc. Rev. 2013; 42: 6723
10c Jacobsen H, Correa A, Poater A, Costabile C, Cavallo L. Coord. Chem. Rev. 2009; 253: 687

11a Gómez-Suárez A, Nelson DJ, Nolan SP. Chem. Commun. 2017; 53: 2650
11b Clavier H, Nolan SP. Chem. Commun. 2010; 46: 841
11c Wuertz S, Glorius F. Acc. Chem. Res. 2008; 41: 1523

12a Yin G, Mu X, Liu G. Acc. Chem. Res. 2016; 49: 2413
12b Yang L, Huang H. Chem. Rev. 2015; 115: 3468
12c 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

13 Dong Z, Ren Z, Thompson SJ, Xu Y, Dong G. Chem. Rev. 2017; 117: 9333
14 Zhao Q, Meng G, Nolan SP, Szostak M. Chem. Rev. 2020; 120: 1981
15 Cai Y, Ye X, Liu S, Shi S.-L. Angew. Chem. Int. Ed. 2019; 58: 13433

16a Tang S, Eisenstein O, Nakao Y, Sakaki S. Organometallics 2017; 36: 2761
16b Guihaumé J, Halbert S, Eisenstein O, Perutz RN. Organometallics 2012; 31: 1300

17a Nakao Y, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2008; 130: 2448
17b Nakao Y, Idei H, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2009; 131: 15996
17c Kanyiva KS, Löbermann F, Nakao Y, Hiyama T. Tetrahedron Lett. 2009; 50: 3463

18 Tsai C.-C, Shih W.-C, Fang C.-H, Li C.-Y, Ong T.-G, Yap GP. A. J. Am. Chem. Soc. 2010; 132: 11887
19 Singh V, Nakao Y, Sakaki S, Deshmukh MM. J. Org. Chem. 2017; 82: 289
20 Yu M.-S, Lee W.-C, Chen C.-H, Tsai F.-Y, Ong T.-G. Org. Lett. 2014; 16: 4826
21 Liu CY, Chen YH, Chen CH, Yu MS, Tsai FY, Ong TG. Synthesis 2016; 48: 2781
22 Zhang T, Luan Y.-X, Lam NY. S, Li J.-F, Li Y, Ye M, Yu J.-Q. Nat. Chem. 2021; 13: 1207
23 Nakao Y, Kashihara N, Kanyiva KS, Hiyama T. Angew. Chem. Int. Ed. 2010; 49: 4451
24 Shih WC, Chen WC, Lai YC, Yu MS, Ho JJ, Yap GP. A, Ong TG. Org. Lett. 2012; 14: 2046
25 Chen WC, Lai YC, Shih WC, Yu MS, Yap GP. A, Ong TG. Chem. Eur. J. 2014; 20: 8099
26 Lee WC, Wang CH, Lin YH, Shih WC, Ong TG. Org. Lett. 2013; 15: 5358
27 Lee WC, Chen CH, Liu CY, Yu MS, Lin YH, Ong TG. Chem. Commun. 2015; 51: 17104
28 Nakao Y, Yamada Y, Kashihara N, Hiyama T. J. Am. Chem. Soc. 2010; 132: 13666
29 Tamura R, Yamada Y, Nakao Y, Hiyama T. Angew. Chem. Int. Ed. 2012; 51: 5679
30 Itahara T, Ouseto F. Synthesis 1984; 488
31 Okumura S, Tang SW, Saito T, Semba K, Sakaki S, Nakao Y. J. Am. Chem. Soc. 2016; 138: 14699
32 Okumura S, Komine T, Shigeki E, Semba K, Nakao Y. Angew. Chem. Int. Ed. 2018; 57: 929
33 Okumura S, Nakao Y. Org. Lett. 2017; 19: 584
34 Donets PA, Cramer N. Angew. Chem. Int. Ed. 2015; 54: 633
35 Li J.-F, Xu W.-W, Wang R.-H, Li Y, Yin G, Ye M. Nat. Commun. 2021; 12: 3070

36a Wang Y.-X, Qi S.-L, Luan Y.-X, Han X.-W, Wang S, Chen H, Ye M. J. Am. Chem. Soc. 2018; 140: 5360
36b Chen H, Wang Y.-X, Luan Y.-X, Ye M. Angew. Chem. Int. Ed. 2020; 59: 9428
36c Yin G, Li Y, Wang R.-H, Li J.-F, Xu X.-T, Luan Y.-X, Ye M. ACS Catal. 2021; 11: 4606
36d Li J.-F, Pan D, Wang H.-R, Zhang T, Li Y, Huang G, Ye M. J. Am. Chem. Soc. 2022; 144: 18810
36e Qi S.-L, Liu Y.-P, Li Y, Luan Y.-X, Ye M. Nat. Commun. 2022; 13: 2938

37a Larsen AO, Leu W, Oberhuber CN, Campbell JE, Hoveyda AH. J. Am. Chem. Soc. 2004; 126: 11130
37b Takatsu K, Shintani R, Hayashi T. Angew. Chem. Int. Ed. 2011; 50: 5548
37c Harada A, Makida Y, Sato T, Ohmiya H, Sawamura M. J. Am. Chem. Soc. 2014; 136: 13932

38 Jiang B, Liu J.-M, Shi S.-L. ACS Catal. 2023; 13: 6068

39a Lewis JC, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2007; 129: 5332
39b Guan B, Hou Z. J. Am. Chem. Soc. 2011; 133: 18086

40a Hara N, Saito T, Semba K, Kuriakose N, Zheng H, Sakaki S, Nakao Y. J. Am. Chem. Soc. 2018; 140: 7070
40b Hara N, Aso K, Li Q.-Z, Sakaki S, Nakao Y. Tetrahedron 2021; 95: 132339

41a Sun X.-Y, Yao B.-Y, Xuan B, Xiao L.-J, Zhou Q.-L. Chem. Catal. 2022; 2: 3140
41b Jiang B, Shi S.-L. Chin. J. Chem. 2022; 40: 1813
41c Liu C.-F, Wang Z.-C, Luo X, Lu J, Ko CH. M, Shi S.-L, Koh MJ. Nat. Catal. 2022; 5: 934

42a Nakao Y, Ebata S, Yada A, Hiyama T, Ikawa M, Ogoshi S. J. Am. Chem. Soc. 2008; 130: 12874
42b Hsieh JC, Ebata S, Nakao Y, Hiyama T. Synlett 2010; 1709

43 Luan Y, Ye M. Chem. Commun. 2022; 58: 12260

44a Diesel J, Finogenova AM, Cramer N. J. Am. Chem. Soc. 2018; 140: 4489
44b Cai Y, Yang X.-T, Zhang S.-Q, Li F, Li Y.-Q, Ruan L.-X, Hong X, Shi S.-L. Angew. Chem. Int. Ed. 2018; 57: 1376

45 Shen D, Zhang WB, Li Z, Shi SL, Xu Y. Adv. Synth. Catal. 2020; 362: 1125
46 Zhang W.-B, Yang X.-T, Ma J.-B, Su Z.-M, Shi S.-L. J. Am. Chem. Soc. 2019; 141: 5634
47 Zhao X, Ma X, Zhu R, Zhang D. Chem. Eur. J. 2020; 26: 5459
48 Ma J.-B, Zhao X, Zhang D, Shi S.-L. J. Am. Chem. Soc. 2022; 144: 13643