Citation: Ruan Liheng, Dong Zhencheng, Chen Chunxin, Wu Shuang, Sun Jing. Recent Progress on the Nickel/Photoredox Dual Catalysis[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2544-2554. doi: 10.6023/cjoc201704051 shu

Recent Progress on the Nickel/Photoredox Dual Catalysis

College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun 113001

Corresponding author: Wu Shuang, wushuang05715@163.com Sun Jing, sunjing@lnpu.edu.cn
Received Date: 30 April 2017
Revised Date: 5 June 2017
Available Online: 16 October 2017
Fund Project: the Talent Scientific Research Found of Liaoning Shihua University 2016XJJ-006the Fund of Liaoning Provincial Department of Education L2016022Project supported by the Fund of Liaoning Provincial Department of Education (No. L2016022), and the Talent Scientific Research Found of Liaoning Shihua University (No. 2016XJJ-006).

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A dual-catalysis system merging the visible light photoredox with transition metal nickel catalysis enables a new strategy to build the novel carbon-carbon and carbon-heteroatom bond, which are not generally possible via using either photoredox or nickel catalysis alone. This mild, green and promising protocol has attracted the interest of some scientific researchers. In this review, the recent progress of nickel/photoredox dual catalysis is summarized.
- photocatalysis,
- nickel catalysis,
- single electron transfer,
- energy transfer
1. [1]
  Zou, Z.; Ye, J.; Sayama, K.; Arakawa, H. Nature 2001, 414, 625. doi: 10.1038/414625a
2. [2]
  Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77. doi: 10.1126/science.1161976
3. [3]
  Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102. doi: 10.1039/B913880N
4. [4]
  Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886. doi: 10.1021/ja805387f
5. [5]
  Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756. doi: 10.1021/ja9033582
6. [6]
  Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239136.
7. [7]
  Prier, C. K.; Rankic, D. A.; Macmillan, D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r
8. [8]
  Dai, X.; Xu, X.; Li, X. Chin. J. Org. Chem. 2013, 33, 2046(in Chinese).
9. [9]
  Guan, B.; Xu, X.; Wang, H.; Li, X. Chin. J. Org. Chem. 2016, 36, 1564(in Chinese).
10. [10]
  Liu, W.; Zheng, X.; Zeng, J.; Cheng, P. Chin. J. Org. Chem. 2017, 37, 1(in Chinese).
11. [11]
  Cheng, X.; Hu, X.; Lu, Z. Chin. J. Org. Chem. 2017, 37, 251(in Chinese).
12. [12]
  Tan, F.; Xiao, W. Acta Chim. Sinica 2015, 73, 85(in Chinese).
13. [13]
  Ding, K.; Xiao, W.; Wu, L. Acta Chim. Sinica 2017, 75, 5(in Chinese).
14. [14]
  Pei, P.; Zhang, F.; Yi, H.; Lei, A. Acta Chim. Sinica 2017, 75, 15(in Chinese). doi: 10.3969/j.issn.0253-2409.2017.01.003
15. [15]
  Wang, D.; Zhang, L.; Luo, S. Acta Chim. Sinica 2017, 75, 22(in Chinese).
16. [16]
  Zhong, J.; Meng, Q.; Chen, B.; Tung, C.; Wu, L. Acta Chim. Sinica 2017, 75, 34(in Chinese). doi: 10.3969/j.issn.0253-2409.2017.01.006
17. [17]
  Zhang, J. Chen, Y. Acta Chim. Sinica 2017, 75, 41(in Chinese). doi: 10.7503/cjcu20160643
18. [18]
  Roh, G.; Iqbal, N. Cho, E. Chin. J. Chem. 2016, 34, 459. doi: 10.1002/cjoc.201500919
19. [19]
  Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437. doi: 10.1126/science.1255525
20. [20]
  Tellis, J.; Kelly, C.; Primer, D.; Jouffroy, M.; Patel, N.; Molander, G. A. Acc. Chem. Res. 2016, 49, 1429. doi: 10.1021/acs.accounts.6b00214
21. [21]
  Gui, Y.; Sun, L.; Lu, Z.; Yu, D. Org. Chem. Front. 2016, 3, 522. doi: 10.1039/C5QO00437C
22. [22]
  Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257. doi: 10.1021/ja501621q
23. [23]
  Johnston, C. P.; Smith, R. T.; Allmendinger, S.; MacMillan, D. W. C. Nature 2016, 536, 322. doi: 10.1038/nature19056
24. [24]
  Zuo, Z.; Cong, H.; Li, W.; Choi, J.; Fu, G. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2016, 138, 1832. doi: 10.1021/jacs.5b13211
25. [25]
  Le, C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 11938. doi: 10.1021/jacs.5b08304
26. [26]
  Chu, L.; Lipshultz, J. M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 7929. doi: 10.1002/anie.201501908
27. [27]
  Zhang, X.; MacMillan, D. W. C. J. Am. Chem. Soc. 2016, 138, 13862. doi: 10.1021/jacs.6b09533
28. [28]
  Gu, L.; Jin, C.; Liu, J.; Zhang, H.; Yuan, M.; Li, G. Green Chem. 2015, 18, 1201.
29. [29]
  Oderinde, M. S.; Varela-Alvarez, A.; Aquila, B.; Robbins, D. W.; Johannes, J. W. J. Org. Chem. 2015, 80, 7642. doi: 10.1021/acs.joc.5b01193
30. [30]
  Feng, Q.; Tong, R. J. Am. Chem. Soc. 2017, 139, 6177. doi: 10.1021/jacs.7b01462
31. [31]
  Luo, J.; Zhang, J. ACS Catal. 2016, 6, 873. doi: 10.1021/acscatal.5b02204
32. [32]
  Huang, H.; Li, X.; Yu, C.; Zhang, Y.; Mariano, P. S.; Wang, W. Angew. Chem., Int. Ed. 2017, 56, 1500. doi: 10.1002/anie.201610108
33. [33]
  McTiernan, C. D.; Leblanc, X.; Scaiano, J. C. ACS Catal. 2017, 7, 2171. doi: 10.1021/acscatal.6b03687
34. [34]
  Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433. doi: 10.1126/science.1253647
35. [35]
  Khatib, M. E.; Serafim, R. A. M.; Molander, G. A. Angew. Chem., Int. Ed. 2016, 55, 254. doi: 10.1002/anie.201506147
36. [36]
  Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Ko-zlowski, M. C. J. Am. Chem. Soc. 2015, 137, 4896. doi: 10.1021/ja513079r
37. [37]
  Gutierrez-Bonet, A.; Tellis, J. C. Matsui, J. K.; Vara, B. A.; Mo-lander, G. A. ACS Catal. 2016, 6, 8004. doi: 10.1021/acscatal.6b02786
38. [38]
  Tellis, J. C.; Amanu, J.; Molander, G. A. Org. Lett. 2016, 18, 2994. doi: 10.1021/acs.orglett.6b01357
39. [39]
  Ryu, D.; Primer, D. N.; Tellis, J. C.; Molander, G. A. Chem. Eur. J. 2016, 22, 120. doi: 10.1002/chem.201504079
40. [40]
  Yamashita, Y.; Tellis, J. C.; Molander, G. A. Proc. Natl. Acad. Sci. U. S. A. 2015, 112, 12026. doi: 10.1073/pnas.1509715112
41. [41]
  Amani, J.; Molander, G. A. J. Org. Chem. 2017, 82, 1856. doi: 10.1021/acs.joc.6b02897
42. [42]
  Amani, J.; Alam, R.; Badir, S.; Molander, G. A. Org. Lett. 2017, 19, 2426. doi: 10.1021/acs.orglett.7b00989
43. [43]
  Karakaya, I.; Primer, D. N.; Molander, G. A. Org. Lett. 2015, 17, 3294. doi: 10.1021/acs.orglett.5b01463
44. [44]
  Karimi-Nami, R.; Tellis, J. C.; Molander, G. A. Org. Lett. 2016, 18, 2572. doi: 10.1021/acs.orglett.6b00911
45. [45]
  Matsui, J. K.; Molander, G. A. Org. Lett. 2017, 19, 436. doi: 10.1021/acs.orglett.6b03448
46. [46]
  Vara, B. A.; Patel, N. R.; Molander, G. A. ACS Catal. 2017, 7, 3955. doi: 10.1021/acscatal.7b00772
47. [47]
  Stache, E. E.; Rovis, T.; Doyle, A. G. Angew. Chem., Int. Ed. 2017, 56, 3679. doi: 10.1002/anie.201700097
48. [48]
  Corce, V.; Chamoreau, L.; Derat, E.; Coddard, J.; Ollivier, C.; Fensterbank, L. Angew. Chem., Int. Ed. 2015, 54, 11414. doi: 10.1002/anie.201504963
49. [49]
  Jouffroy, M.; Primer, D. N.; Molander, G. A. J. Am. Chem. Soc. 2016, 138, 475. doi: 10.1021/jacs.5b10963
50. [50]
  Patel, N. R.; Kelly, C. B.; Jouffroy, M.; Molander, G. A. Org. Lett. 2016, 18, 764. doi: 10.1021/acs.orglett.6b00024
51. [51]
  Leveque, C.; Corce, V.; Chenneberg, L.; Ollivier, C.; Fensterbank. Eur. J. Org. Chem. 2017, 2017, 2118. doi: 10.1002/ejoc.201601571
52. [52]
  Jouffroy, M.; Davies, G. H.; Molander, G. A. Org. Lett. 2016, 18, 1606. doi: 10.1021/acs.orglett.6b00466
53. [53]
  Patel, N. R.; Molander, G. A. J. Org. Chem. 2016, 81, 7271. doi: 10.1021/acs.joc.6b00800
54. [54]
  Vara, B. A.; Jouffroy, M.; Molander, G. A. Chem. Sci. 2017, 8, 530. doi: 10.1039/C6SC03236B
55. [55]
  Jouffroy, M.; Kelly, C. B.; Molander, G. A. Org. Lett. 2016, 18, 876. doi: 10.1021/acs.orglett.6b00208
56. [56]
  Gutiérrez-Bonet, Á.; Tellis, J. C.; Matsui, J. K.; Vara, B. A.; Molander, G. A. ACS Catal. 2016, 6, 8004. doi: 10.1021/acscatal.6b02786
57. [57]
  Duan, Z.; Li, W.; Lei, A. Org. Lett. 2016, 18, 4012. doi: 10.1021/acs.orglett.6b01837
58. [58]
  Paul, A.; Smith, M.; Vannucci. J. Org. Chem. 2017, 82, 1996. doi: 10.1021/acs.joc.6b02830
59. [59]
  Joe, C. L.; Doyle, A. G. Angew. Chem., Int. Ed. 2016, 55, 4040. doi: 10.1002/anie.201511438
60. [60]
  Shields, B. J.; Doyle, A. G. J. Am. Chem. Soc. 2016, 138, 12719. doi: 10.1021/jacs.6b08397
61. [61]
  Shaw, M. H.; Shurtleff, V. W.; Terrett, J. A.; Cuthbertson, J.D.; MacMillan, D. W. C. Science 2016, 352, 1304. doi: 10.1126/science.aaf6635
62. [62]
  Gui, Y. Y.; Liao, L. L.; Sun, L.; Zhang, Z.; Ye, J. H.; Shen, G.; Lu, Z. P.; Zhou, W. J.; Yu, D. G. Chem. Commun. 2017, 53, 1192. doi: 10.1039/C6CC09685A
63. [63]
  Oderinde, M. S.; Frenette, M.; Robbins, D. W.; Aquila, B.; Johannes, J. W. J. Am. Chem. Soc. 2016, 138, 1760. doi: 10.1021/jacs.5b11244
64. [64]
  Xuan, J.; Zeng, T. T.; Chen, J. R.; Lu, L. Q.; Xiao, W. J. Chem. Eur. J. 2015, 21, 4962. doi: 10.1002/chem.201500227
65. [65]
  Terrett, J. A.; Cuthbertson, J. D.; Shurtleff, V. W.; MacMillan, D. W. C. Nature 2015, 524, 330. doi: 10.1038/nature14875
66. [66]
  Tasker, S. Z.; Jamison, T. F. J. Am. Chem. Soc. 2015, 137, 9531. doi: 10.1021/jacs.5b05597
67. [67]
  Corcoran, E. B.; Piront, M. T.; Lin, S.; Dreher, S. D.; DiRocco, D. A.; Davies, I. W.; Buchwald, S. L.; MacMillan, D. W. C. Science 2016, 353, 279. doi: 10.1126/science.aag0209
68. [68]
  Heitz, D. R.; Tellis, J. C.; Molander, G. A. J. Am. Chem. Soc. 2016, 138, 12715. doi: 10.1021/jacs.6b04789
69. [69]
  Welin, E. R.; Le, C.; Arias-Rotondo, D. M.; McCusker, J. K., MacMillan, D. W. C. Science 2017, 355, 380. doi: 10.1126/science.aal2490
70. [70]
  Ding, W.; Lu, L.; Zhou, Q.; Wei, Y.; Chen, J.; Xiao, W. J. Am. Chem. Soc. 2017, 139, 63. doi: 10.1021/jacs.6b11418
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