Citation: Cheng Lei, Zhou Qilin. Advances on Nickel-Catalyzed C(sp³)-C(sp³) Bond Formation[J]. Acta Chimica Sinica, ;2020, 78(10): 1017-1029. doi: 10.6023/A20070335 shu

Advances on Nickel-Catalyzed C(sp³)-C(sp³) Bond Formation

Cheng Lei ,
Zhou Qilin ^,

Institute of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Zhou Qilin, qlzhou@nankai.edu.cn
Received Date: 29 July 2020
Available Online: 15 September 2020
Fund Project: the National Natural Science Foundation of China 21790330Project supported by the National Natural Science Foundation of China (Nos. 21790332, 21790330)the National Natural Science Foundation of China 21790332

Figures(36)

Transition metal-catalyzed coupling reactions are powerful synthetic methods for the C-C bond formation. Many coupling reactions such as Heck reaction, Negishi coupling, and Suzuki coupling have been widely applied in the syntheses of pharmaceuticals, functional materials and fine chemicals. In those coupling reactions, a C(sp²)-C(sp²) bond is formed in high efficiency and selectivity. However, in contrast to the C(sp²)-C(sp²) couplings, the C(sp³)-C(sp³) couplings are more difficult and develop late. Because the C(sp³)-C(sp³) bonds are ubiquitous in organic compound, the C(sp³)-C(sp³) bond formation is the central task of research in organic chemistry. In the past two decades, a great effort has been devoted to the development of cross-coupling reactions between alkyls to construct C(sp³)-C(sp³) bonds and impressive progress has been achieved. Among the transition metal catalysts that have been used in the construction of C(sp³)-C(sp³) bonds, nickel was found to be a preferable one, exhibiting unique activity and selectivity. Nickel catalysts promote the activation of alkyl electrophiles via radical catalytic cycles and inhibit and/or manipulate β-H elimination reactions. Nickel has several variable valence states and can flexibly participate in tandem reactions and reductive cross-coupling reactions. All these characteristic natures contribute to the success of nickel catalysts in the construction of C(sp³)-C(sp³) bonds. In this review, we will describe the advances on the nickel-catalyzed C(sp³)-C(sp³) bond-forming reactions. The main contents of this review include:the cross-coupling of alkyl electrophiles with organometallic reagents; the coupling involving a C(sp³)-H bond activation in the presence of directing group; the coupling co-catalyzed by nickel and photocatalyst; the reductive coupling of two alkyl electrophiles; and the additions of nucleophiles or electrophiles to alkenes such as hydroalkylation and difunctionalization of alkenes. The review will focus on the latest developments of nickel-catalyzed alkyl coupling reactions in the past two decades. The mechanisms of each reaction are discussed in detail for understanding the reactions.
- nickel catalysis,
- C(sp³)-C(sp³) bond formation,
- cross-coupling,
- addition reactions of olefins,
- asymmetric synthesis
1. [1]
  For reviews on nickel catalysis: (a) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature, 2014, 509, 299. (b) Ananikov, V. P. ACS Catal. 2015, 5, 1964. (c) Clevenger, A. L.; Stolley, R. M.; Aderibigbe, J.; Louie, J. Chem. Rev. 2020, 120, 6124. (d) Choi, J.; Fu, G. C. Science 2017, 356, eaaf7230. (e) Modern Organonickel Chemistry, Eds.: Tamaru, Y., Wiley-VCH, Weinheim, 2005. (f) Nickel Catalysis in Organic Synthesis: Methods and Reactions, Eds.: Ogoshi, S., Wiley-VCH, Weinheim, 2020.
2. [2]
  Devasagayaraj, A.; Stüdemann, T.; Knochel, P. Angew. Chem. Int. Ed. 1996, 34, 2723. doi: 10.1002/anie.199527231
3. [3]
  (a) Giovannini, R.; Stüdemann, T.; Dussin, G.; Knochel, P. Angew. Chem. Int. Ed. 1998, 37, 2387. (b) Giovannini, R.; Stüdemann, T.; Devasagayaraj, A.; Dussin, G.; Knochel, P. J. Org. Chem. 1999, 64, 3544. (c) Piber, M.; Jensen, A. E.; Rottl nder, M.; Knochel, P. Org. Lett. 1999, 1, 1323.
4. [4]
  Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222. doi: 10.1021/ja025828v
5. [5]
  Hills, I. D.; Netherton, M. R.; Fu, G. C. Angew. Chem. Int. Ed. 2003, 42, 5749. doi: 10.1002/anie.200352858
6. [6]
  Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726. doi: 10.1021/ja0389366
7. [7]
  (a) Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2007, 129, 9602. (b) Smith, S. W.; Fu, G. C. Angew. Chem. Int. Ed. 2008, 47, 9334. (c) Vechorkin, O.; Hu, X. Angew. Chem. Int. Ed. 2009, 48, 2937.
8. [8]
  Fisher, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 4594. doi: 10.1021/ja0506509
9. [9]
  Binder, J. T.; Cordier, C. J.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 17003. doi: 10.1021/ja308460z
10. [10]
  (a) Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 10482. (b) Son, S.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 2756. (c) Lundin, P. M.; Esquivias, J.; Fu, G. C. Angew. Chem. Int. Ed. 2009, 48, 154. (d) Smith, S. W.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 12645. (e) Liang, Y.; Fu, G. C. J. Am. Chem. Soc. 2014, 136, 5520. (f) Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 11908. (g) Lu, Z.; Wilsily, A.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 8154. (h) Wilsily, A.; Tramutola, F.; Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 5794. (i) Huo, H.; Gorsline, B. J.; Fu, G. C. Science 2020, 367, 559.
11. [11]
  Schmidt, J.; Choi, J.; Liu, A. T.; Slusarczyk, M.; Fu, G. C. Science, 2016, 354, 1265. doi: 10.1126/science.aai8611
12. [12]
  Schwarzwalder, G. M.; Matier, C. D.; Fu, G. C. Angew. Chem. Int. Ed. 2019, 58, 3571. doi: 10.1002/anie.201814208
13. [13]
  Breitenfeld, J.; Ruiz, J.; Wodrich, M. D.; Hu, X. J. Am. Chem. Soc. 2013, 135, 12004. doi: 10.1021/ja4051923
14. [14]
  Schley, N. D.; Fu, G. C. J. Am. Chem. Soc. 2014, 136, 16588. doi: 10.1021/ja508718m
15. [15]
  Hu, X. Chem. Sci. 2011, 2, 1867.
16. [16]
  (a) Tollefson, E. J.; Hanna, L. E.; Jarvo, E. R. Acc. Chem. Res. 2015, 48, 2344. (b) Su, B.; Cao, Z.-C.; Shi, Z.-J. Acc. Chem. Res. 2015, 48, 886.
17. [17]
  (a) Guan, B.-T.; X, S.-K.; Wang, B.-Q.; Sun, Z.-P.; Wang, Y.; Zhao, K.-Q.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 3268. (b) Yu, D.-G.; Wang, X.; Zhu, R.-L.; Luo, S.; Wang, B.-Q.; Wang, L.; Shi, Z.-J. J. Am. Chem. Soc. 2012, 134, 14638.
18. [18]
  Taylor, B. L. H.; Swift, E. C.; Waetzig, J. D.; Jarvo, E. R. J. Am. Chem. Soc. 2011, 133, 389. doi: 10.1021/ja108547u
19. [19]
  Qin, T.; Cornella, J.; Li, C.; Malins, L. R.; Edwards, J. T.; Kawamura, S.; Maxwell, B. D.; Eastgate, M. D.; Baran, P. S. Science 2016, 352, 801. doi: 10.1126/science.aaf6123
20. [20]
  Plunkett, S.; Basch, C. H.; Santana, S. O.; Watson, M. P. J. Am. Chem. Soc. 2019, 141, 2257. doi: 10.1021/jacs.9b00111
21. [21]
  Zhan, B.-B.; Liu, B.; Hu, F.; Shi, B.-F. Sci. Chin. Chem. 2015, 60, 2097(in Chinese).
22. [22]
  Wu, X.; Zhao, Y.; Ge, H. J. Am. Chem. Soc. 2014, 136, 1789. doi: 10.1021/ja413131m
23. [23]
  (a) Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437. (b) Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433.
24. [24]
  (a) Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.; Evans, R. W.; MacMillan, D. W. C. Nat. Rev. Chem. 2017, 1, 0052. (b) Tells, J. C.; Kelly, C. B.; Primer, D.V.; Jouffroy, M.; Patel, N. R.; Molander, G. A. Acc. Chem. Res. 2016, 49, 1429. (c) Milligan, J. A.; Phelan, J. P.; Badir, S. O.; Molander, G. A. Angew. Chem. Int. Ed. 2019, 58, 6152.
25. [25]
  Johnston, C. P.; Smith, R. T.; Allmendinger, S.; MacMillan, D. W. C. Nature 2016, 536, 322. doi: 10.1038/nature19056
26. [26]
  Le, C.; Liang, Y.; Evans, R. W.; Li, X.; MacMillan, D. W. C. Nature 2017, 547, 79. doi: 10.1038/nature22813
27. [27]
  Smith, R. T.; Zhang, X.; Rincón, J. A.; Agejas, J.; Mateos, C.; Barberis, M.; García-Cerrada, S.; Frutos, O. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2018, 140, 17433. doi: 10.1021/jacs.8b12025
28. [28]
  For selected reviews of reductive cross-couplings: (a) Knappke, C. E. I.; Grupe, S.; G rtner, D.; Corpet, M.; Gosmini, C.; Jacobi von Wangelin, A. Chem. Eur. J. 2014, 20, 6828. (b) Gu, J.; Wang, X.; Xue, W.; Gong, H. Org. Chem. Front. 2015, 2, 1411. (c) Wang, X.; Dai, Y.; Gong, H. Top. Curr. Chem. 2016, 374, 43. (d) Lucas, E. L.; Jarvo, E. R. Nat. Rev. Chem. 2017, 1, No. 0065. (e) Poremba, K. E.; Dibrell, S. E.; Reisman, S. E. ACS Catal. 2020, 10, 8237.
29. [29]
  Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Org. Lett. 2011, 13, 2138. doi: 10.1021/ol200617f
30. [30]
  Xu, H.; Zhao, C.; Qian, Q.; Deng, W.; Gong, H. Chem. Sci. 2013, 4, 4022. doi: 10.1039/c3sc51098k
31. [31]
  Komeyama, K.; Michiyuki, T.; Osaka, I. ACS Catal. 2019, 9, 9285. doi: 10.1021/acscatal.9b03352
32. [32]
  (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (c) McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981. (d) Dong, Z.; Ren, Z.; Thompson, S. J.; Xu, Y.; Dong, G. Chem. Rev. 2017, 117, 9333. (e) Yan, T.; Guironnet, D. Sci. Chin. Chem. 2020, 63, 755.
33. [33]
  Wang, X.-X.; Lu, X.; Li. Y.; Wang, J.-W.; Fu, Y. Sci Chin. Chem.10.1007/s11426-020-9838-x. doi: 10.1007/s11426-020-9838-x
34. [34]
  Lu, X.; Xiao, B.; Zhang, Z.-Q.; Gong, T.-J.; Su, W.; Yi, J.; Fu, Y.; Liu, L. Nat. Commun. 2016, 7, 11129. doi: 10.1038/ncomms11129
35. [35]
  Zhou, F.; Zhu, J.; Zhang, Y.; Zhu, S. Angew. Chem. Int Ed. 2018, 57, 4058. doi: 10.1002/anie.201712731
36. [36]
  Wang, Z.-Y.; Wan, J.-H.; Wang, G.-Y.; Wang, R.; Jin, R.-X.; Lan, Q.; Wang, X.-S. Tetrahedron Lett. 2018, 59, 2302. doi: 10.1016/j.tetlet.2018.05.008
37. [37]
  (a) Sun, S.-Z.; Borjesson, M.; Martin-Montero, R.; Martin, R. J. Am. Chem. Soc. 2018, 140, 12765. (b) Qian, D.; Hu, X. Angew. Chem. Int. Ed. 2019, 58, 18519.
38. [38]
  Lu, X.; Xiao, B.; Liu, L.; Fu, Y. Chem. Eur. J. 2016, 22, 11161. doi: 10.1002/chem.201602486
39. [39]
  Sun, S.-Z.; Romano, C.; Martin, R. J. Am. Chem. Soc. 2019, 141, 16197. doi: 10.1021/jacs.9b07489
40. [40]
  Wang, Z.; Yin, H.; Fu, G. C. Nature 2018, 563, 379. doi: 10.1038/s41586-018-0669-y
41. [41]
  Zhou, F.; Zhang, Y.; Xu, X.; Zhu, S. Angew. Chem. Int. Ed. 2019, 58, 1754. doi: 10.1002/anie.201813222
42. [42]
  He, S.-J.; Wang, J.-W.; Li, Y.; Xu, Z.-Y.; Wang, X.-X.; Lu, X.; Fu, Y. J. Am. Chem. Soc. 2020, 142, 214. doi: 10.1021/jacs.9b09415
43. [43]
  Yang, Z.-P.; Fu, G. C. J. Am. Chem. Soc. 2020, 142, 5870. doi: 10.1021/jacs.0c01324
44. [44]
  Green, S. A.; Huffman, T. R.; McCourt, R. O.; van der Puyl, V.; Shenvi, R. A. J. Am. Chem. Soc. 2019, 141, 7709. doi: 10.1021/jacs.9b02844
45. [45]
  Cheng, L.; Li, M.-M.; Xiao, L.-J.; Xie, J.-H.; Zhou, Q.-L. J. Am. Chem. Soc. 2018, 140, 11627. doi: 10.1021/jacs.8b09346
46. [46]
  Chen, T.; Yang, H.; Yang, Y.; Dong, G.; Xing, D. ACS Catal. 2020, 10, 4238. doi: 10.1021/acscatal.0c00019
47. [47]
  (a) Cheng, L.; Li, M.-M.; Wang, B.; Xiao, L.-J.; Xie, J.-H.; Zhou, Q.-L. Chem. Sci. 2019, 10, 10417. (b) Lv, L.; Zhu, D.; Qiu, Z.; Li, J.; Li, C.-J. ACS Catal. 2019, 9, 9199.
48. [48]
  Ji, D.-W.; He, G.-C.; Zhang, W.-S.; Zhao, C.-Y.; Hu, Y.-C.; Chen, Q.-A. Chem. Commun. 2020, 56, 7431. doi: 10.1039/D0CC02697B
49. [49]
  (a) Dhungana, R. K.; KC, S.; Basnet, P.; Giri, R. Chem. Rec. 2018, 18, 1314. (b) Giri, R.; KC, S. J. Org. Chem. 2018, 83, 3013. (c) Derosa, J.; Apolinar, O.; Kang, T.; Tran, V. T.; Engle, K. M. Chem. Sci. 2020, 11, 4287. (d) Luo, Y.-C.; Xu, C.; Zhang, X. Chin. J. Chem. 2020, 38, 1371. (e) Qi, X.; Diao, T. ACS Catal. 2020, 10, 8542.
50. [50]
  Qin, T.; Cornella, J.; Li, C.; Malins, L. R.; Edwards, J. T.; Kawamura, S.; Maxwell, B. D.; Eastage, M. D.; Baran, P. S. Science, 2016, 352, 801. doi: 10.1126/science.aaf6123
51. [51]
  KC, S.; Dhungana, R. K.; Shrestha, B.; Thapa, S.; Khanal, N.; Basnet, P.; Lebrun, R. W.; Giri, R. J. Am. Chem. Soc. 2018, 140, 9801. doi: 10.1021/jacs.8b05374
52. [52]
  Chierchia, M.; Xu, P.; Lovinger, G. J.; Morken, J. P. Angew. Chem. Int. Ed. 2019, 58, 14245. doi: 10.1002/anie.201908029
53. [53]
  García-Domínguez, A.; Li, Z.; Nevado, C. J. Am. Chem. Soc. 2017, 139, 6835. doi: 10.1021/jacs.7b03195
54. [54]
  Shu, W.; García-Domínguez, A.; Quirós, M. T.; Mondal, R.; Cárdenas, D. J.; Nevado, C. J. Am. Chem. Soc. 2019, 141, 13812. doi: 10.1021/jacs.9b02973
55. [55]
  (a) Guo, L.; Tu, H.-Y.; Zhu, S.; Chu, L. Org. Lett. 2019, 21, 4771. (b) García-Domínguez, A.; Mondal, R.; Nevado, C. Angew. Chem. Int. Ed. 2019, 58, 12286. (c) Campbell, M. W.; Compton, J. S.; Kelly, C. B.; Molander, G. A. J. Am. Chem. Soc. 2019, 141, 20069.
56. [56]
  Derosa, J.; Tran, V. T.; Boulous, M. N.; Chen, J. S.; Engle, K. M. J. Am. Chem. Soc. 2017, 139, 10657. doi: 10.1021/jacs.7b06567
57. [57]
  Derosa, J.; van der Puyl, V. A.; Tran, V. T.; Liu, M.; Engle, K. M. Chem. Sci. 2018, 9, 5278. doi: 10.1039/C8SC01735B
58. [58]
  (a) Nattmann, L.; Saeb, R.; N thling, N.; Cornella, J. Nat. Catal. 2020, 3, 6. (b) Tran, V. T.; Li, Z.-Q.; Apolinar, O.; Derosa, J.; Joannou, . W. V.; Wisniewski, S. R.; Eastgate, M. D.; Engle, K. M. Angew. Chem. Int. Ed. 2020, 59, 7409.
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Advances on Nickel-Catalyzed C(sp³)-C(sp³) Bond Formation