Citation: Liu Yuanlie, Wang Mei, Chen Lei, Li Dashan, Wang Wenjing, Zhan Rui, Shao Lidong. Progress in α-C(sp³)-H Arylation of Cyclic Compounds with Carbonyl Groups[J]. Chemistry, ;2020, 83(7): 641-651. shu

Progress in α-C(sp³)-H Arylation of Cyclic Compounds with Carbonyl Groups

Liu Yuanlie ¹ ,
Wang Mei ² ,
Chen Lei ² ,
Li Dashan ² ,
Wang Wenjing ² ,
Zhan Rui ^1,, ,
Shao Lidong ^2,,

1.
School of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, 650500
2.
School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650500

Corresponding author: Zhan Rui, sunnyzhanrui@126.com Shao Lidong, shaolidong@ynutcm.edu.cn
Received Date: 2 December 2019
Accepted Date: 2 March 2020

Figures(13)

Cyclic compounds with carbonyl groups comprise of cyclic ketones, lactones, and lactams. The α-C(sp³)-H arylation of these cyclic compounds is an important type of C-H functionalization, exhibiting high efficiency in formation of C(sp³)-C(sp²) bonds, playing an important role in organic synthesis, and attracting majority of interests from organic and medicinal communities. Up to now, various α-C(sp³)-H arylations of these cyclic compounds have been reported. This article mainly reviews the research progress of such reactions in the past two decades.
- α-C(sp³)-H arylation,
- C-H functionalization,
- Cyclic compounds with carbonyl groups
1. [1]
  Ren J, Shi X, Li X N, et al. Org. Lett., 2016, 18(16):3948~3951.
2. [2]
  Zhu Y, Shao L D, Deng Z T, et al. J. Org. Chem., 2018, 83(17):10166~10174.
3. [3]
  Xu J, Shao L D, Li D S, et al. J. Am. Chem. Soc., 2014, 136(52):17962~17965.
4. [4]
  Godula K, Sames D. Science, 2006, 312(5770):67~72.
5. [5]
  He J, Wasa M, Chan K S L, et al. Chem. Rev., 2017, 117(13):8754~8786.
6. [6]
  Vargová D, Némethová L, Plevová K, et al. ACS Catal., 2019, 9(4):3104~3143.
7. [7]
  Murahashi T, Kurosawa H. J. Organomet. Chem., 1999, 574(1):142~147.
8. [8]
  Ciufolini M A, Qi H B, Browne M E. J. Org. Chem., 1988, 53(17):4149~4151.
9. [9]
  Muratake H, Natsume M. Tetrahed. Lett., 1997, 38(43):7581~7582.
10. [10]
  Palucki M, Buchwald S L. J. Am. Chem. Soc., 1997, 119(45):11108~11109.
11. [11]
  Svennebring A, Garg N, Nilsson P, et al. J. Org. Chem., 2005, 70(12):4720~4725.
12. [12]
  Storgaard M, Dörwald F Z, Peschke B, et al. J. Org. Chem., 2009, 74(14):5032~5040.
13. [13]
  Bélanger É, Cantin K, Messe O, et al. J. Am. Chem. Soc., 2007, 129(5):1034~1035.
14. [14]
  Solé D, Vallverdú L, Solans X, et al. J. Am. Chem. Soc., 2003, 125(6):1587~1594.
15. [15]
  Huang Z, Chen Z L, Lim L H, et al. Angew. Chem. Int. Ed., 2013, 52(22):5807~5812.
16. [16]
  hman J, Wolfe J P, Troustman M V, et al. J. Am. Chem. Soc., 1998, 120(8):1918~1919.
17. [17]
  Kawatsura M, Hartwig J F. J. Am. Chem. Soc., 1999, 121(7):1473~1478.
18. [18]
  Fox J M, Huang X H, Chieffi A, et al. J. Am. Chem. Soc., 2000, 122(7):1360~1370.
19. [19]
  Ehrentraut A, Zapf A, Beller M. Adv. Synth. Catal., 2002, 344(2):209~217.
20. [20]
  Liao X, Weng Z, Hartwig J F. J. Am. Chem. Soc., 2008, 130(1):195~200.
21. [21]
  Viciu M S, Germaneau R F, Nolan S P. Org. Lett., 2002, 4(23):4053~4056.
22. [22]
  Hamada T, Chieffi A, Åhman J, et al. J. Am. Chem. Soc., 2002, 124(7):1261~1268.
23. [23]
  Liao X, Stanley L M, Hartwig J F. J. Am. Chem. Soc., 2011, 133(7):2088~2091.
24. [24]
  Han C, Kim E H, Colby D A. J. Am. Chem. Soc., 2011, 133(15):5802~5805.
25. [25]
  Jiao Z W, Beiger J J, Jin Y S, et al. J. Am. Chem. Soc., 2016, 138(49):15980~15986.
26. [26]
  Shaughnessy K H, Hamann B C, Hartwig J F. J. Org. Chem., 1998, 63(19):6546~6553.
27. [27]
  Durbin M J, Willis M C. Org. Lett., 2008, 10(7):1413~1415.
28. [28]
  Altman R A, Hyde A M, Huang X H, et al. J. Am. Chem. Soc., 2008, 130(29):9613~9620.
29. [29]
  Taylor A M, Altman R A, Buchwald S L. J. Am. Chem. Soc., 2009, 131(29):9900~9901.
30. [30]
  Jin Y S, Chen M, Ge S Z, et al. Org. Lett., 2017, 19(6):1390~1393.
31. [31]
  Xu Y, Su T S, Huang Z X, et al. Angew. Chem. Int. Ed., 2016, 55(7):2559~2563.
32. [32]
  Liu R R, Li B L, Lu J, et al. J. Am. Chem. Soc., 2016, 138(16):5198~5201.
33. [33]
  Zhu C D, Wang D Y, Sun W Y, et al. J. Am. Chem. Soc., 2017, 139(46):16486~16489.
34. [34]
  Huang X, Oh W R J J, Zhou J S. Angew. Chem. Int. Ed., 2018, 57(26):7673~7677.
35. [35]
  Wang M, Chen J, Chen Z J, et al. Angew. Chem. Int. Ed., 2018, 57(10):2707~2711.
36. [36]
  Liu X, Hartwig J F. Org. Lett., 2003, 5(11):1915~1918.
37. [37]
  Jiang L, Weist S, Jansat S. Org. Lett., 2009, 11(7):1543~1546.
38. [38]
  Fernández-Nieto F, Mas Roselló J, Lenoir S, et al. Org. Lett., 2015, 17(15):3838~3841.
39. [39]
  Hyde A M, Buchwald S L. Angew. Chem. Int. Ed., 2008, 47(1):177~180.
40. [40]
  Zhao Y H, Zhou Y Y, Liang L L, et al. Org. Lett., 2009, 11(3):555~558.
41. [41]
  Johnson T, Pultar F, Menke F, et al. Org. Lett., 2016, 18(24):6488~6491.
42. [42]
  Hou W Y, Wu Y K. Org. Lett., 2017, 19(5):1220~1223.
43. [43]
  Yang Y C, Lin Y C, Wu Y K. Org. Lett., 2019, 21(23):9286~9290.
44. [44]
  Semmelhack M F, Stauffer R D, Rogerson T D. Tetrahed. Lett., 1973, 14(45):4519~4522.
45. [45]
  Spielvogel D J, Buchwald S L. J. Am. Chem. Soc., 2002, 124(14):3500~3501.
46. [46]
  Chen G S, Kwong F Y, Chan H O, et al. Chem. Commun., 2006, (13):1413~1415.
47. [47]
  Ge S, Hartwig J F. J. Am. Chem. Soc., 2011, 133(41):16330~16333.
48. [48]
  Josep C, Jackson E P, Martin R. Angew. Chem. Int. Ed., 2015, 54(13):4075~4078.
49. [49]
  Ghosh A, Walker J A, Arkady A, et al. ACS Catal., 2016, 6(4):2673~2680.
50. [50]
  Harvey J S, Simonovich S P, Jamison C R, et al. J. Am. Chem. Soc., 2011, 133(35):13782~13785.
51. [51]
  Liu T, Feng J J, Chen C, et al. Org. Lett., 2019, 21(12):4505~4509.
52. [52]
  Baran P S, Richter J M. J. Am. Chem. Soc., 2004, 126(24):7450~7451.
53. [53]
  Baran P S, Richter J M. J. Am. Chem. Soc., 2005, 127(44):15394~15396.
54. [54]
  Baran P S, Maimone T J, Richter J M. Nature, 2007, 446(7134):404~408.
55. [55]
  Wu H R, Huang H Y, Ren C L, et al. Chem. Eur. J., 2015, 21(47):16744~16748.
56. [56]
  Guo J, Dong S X, Zhang Y L, et al. Angew. Chem. Int. Ed., 2013, 52(39):10245~10249.
57. [57]
  Ueda N, Tokuyama T, Sakan T. Bull. Chem. Soc. Jpn., 1966, 39(9):2012~2014.
58. [58]
  Stewart J D, Fields S C, Kochhar K S, et al. J. Org. Chem., 1987, 52(10):2110~2113.
59. [59]
  Picazo E, Anthony S M, Giroud M, et al. J. Am. Chem. Soc., 2018, 140(24):7605~7610.
60. [60]
  Semmelhack M F, Bargar T M. J. Org. Chem., 1977, 42(8):1481~1482.
61. [61]
  Liang K, Li N, Zhang Y, et al. Chem. Sci., 2019, 10(10):3049~3053.
62. [62]
  Shirakawa S, Koga K, Takuda T, et al. Angew. Chem. Int. Ed., 2014, 53(24):6220~6223.
63. [63]
  Sattar M, Rathore V, Prasad C D, et al. Chem. Asian J., 2017, 12(7):734~743.
64. [64]
  Rao X F, Li N K, Bai H, et al. Angew. Chem. Int. Ed., 2018, 57(38):12328~12332.
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Progress in α-C(sp3)-H Arylation of Cyclic Compounds with Carbonyl Groups

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通讯作者: 陈斌, bchen63@163.com

Progress in α-C(sp³)-H Arylation of Cyclic Compounds with Carbonyl Groups