Citation: Huang Yuanting, Chen Qian. Recent Progress in P- and S-Arylation Reactions of Arynes[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4087-4100. doi: 10.6023/cjoc202005047 shu

Recent Progress in P- and S-Arylation Reactions of Arynes

Huang Yuanting ,
Chen Qian ^,

School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006

Corresponding author: Chen Qian, qianchen@gdut.edu.cn
Received Date: 18 May 2020
Revised Date: 21 June 2020
Available Online: 15 July 2020
Fund Project: the Basic and Applied Basic Research Foundation of Guangdong Province 2019B1515120035the 100 Young Talents Programme of Guangdong University of Technology 220413506the Science and Technology Planning Project of Guangdong Province 2017A010103044Project supported by the Science and Technology Planning Project of Guangdong Province (No. 2017A010103044), the 100 Young Talents Programme of Guangdong University of Technology (No. 220413506) and the Basic and Applied Basic Research Foundation of Guangdong Province (No. 2019B1515120035)

Figures(31)

Arylphosphine and aryl sulfur compounds have been widely used in organic synthesis, functional materials and pharmaceutical chemistry. Thus, the development of green, mild and highly efficient methodologies for P- and S-arylation is of great importance. Recently, the reactions involving arynes provided a novel approach to the arylation of organophosphorus and organosulfur compounds. These reactions can be performed in the absence of transition metal catalysts under mild conditions with broad scope. The recent progress in P- and S-arylation reactions with arynes is introduced on the basis of different reaction types.
- aryne,
- organophosphorus,
- organosulfur,
- arylation reaction
1. [1]
  (a) Demmer, C. S.; Krogsgaard-Larsen, N.; Bunch, L. Chem. Rev. 2011, 111, 7981.
  (b) Montchamp, J.-L. Acc. Chem. Res. 2014, 47, 77.
  (c) Zhang, J.; Ding, D.; Wei, Y.; Xu, H. Chem. Sci. 2016, 7, 2870.
  (d) Joachimiak, Ł.; Błażewska, K. M. J. Med. Chem. 2018, 61, 8536.
2. [2]
3. [3]
  (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
  (b) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461.
4. [4]
  (a) Rueeger, H.; Lueoend, R.; Rogel, O.; Rondeau, J.-M.; Möbitz, H.; Machauer, R.; Jacobson, L.; Staufenbiel, M.; Desrayaud, S.; Neumann, U. J. Med. Chem. 2012, 55, 3364.
  (b)Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.
5. [5]
6. [6]
7. [7]
  (a) Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502.
  (b) Okuma, K. Heterocycles 2012, 85, 515.
  (c) Bhojgude, S. S.; Biju, A. T. Angew. Chem., Int. Ed. 2012, 51, 1520.
  (d) Wu, C.; Shi, F. Asian J. Org. Chem. 2013, 2, 116.
  (e) Modha, S. G.; Mehta, V. P.; Van der Eycken, E. V. Chem. Soc. Rev. 2013, 42, 5042.
8. [8]
  Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 12, 1211.
9. [9]
  Matsuzawa, T.; Yoshida, S.; Hosoya, T. Tetrahedron Lett. 2018, 59, 4197.
10. [10]
  (a) Chen, L.; Zhang, C.; Wen, C.; Zhang, K.; Liu, W.; Chen, Q. Catal. Commun. 2015, 65, 81.
  (b) Chen, Q.; Zhang, C.; Chen, L.; Wen, C.; Du, Z.; Chen, H.; Zhang, K. Tetrahedron Lett. 2015, 56, 2094.
  (c) Wen, C.; Chen, Q.; He, Z.; Yan, X.; Zhang, C.; Du, Z.; Zhang, K. Tetrahedron Lett. 2015, 56, 5470.
  (d) Chen, Q.; Yan, X.; Du, Z.; Zhang, K.; Wen, C. J. Org. Chem. 2016, 81, 276.
  (e) Chen, Q.; Yan, X.; Wen, C.; Zeng, J.; Huang, Y.; Liu, X.; Zhang, K. J. Org. Chem. 2016, 81, 9476.
11. [11]
  Rémond, E.; Tessier, A.; Leroux, F. R.; Bayardon, J.; Jugé, S. Org. Lett. 2010, 12, 1568.
12. [12]
  Yoshida, S.; Uchida, K.; Igawa, K.; Tomooka, K.; Hosoya, T. Chem. Commun. 2014, 50, 15059.
13. [13]
  Dhokale, R. A.; Mhaske, S. B. Org. Lett. 2013, 15, 2218.
14. [14]
  Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307.
15. [15]
  Yoshida, S.; Hosoya, T. Chem. Lett. 2013, 42, 583.
16. [16]
  Yang, G.; Shen, C.; Quan, M.; Zhang, W. Tetrahedron 2016, 72, 333.
17. [17]
  Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Chem. Lett. 2005, 34, 1538.
18. [18]
  Alajarin, M.; Lopez-Leonardo, C.; Raja, R.; Orenes, R. Org. Lett. 2011, 13, 5668.
19. [19]
  Lopez-Leonardo, C.; Raja, R.; López-Ortiz, F.; del Águila-Sánchez, M. Á.; Alajarin, M. Eur. J. Org. Chem. 2014, 1084.
20. [20]
  Shen, C.; Yang, G.; Zhang, W. Org. Lett. 2013, 15, 5722.
21. [21]
  Qi, N.; Zhang, N.; Allu, S. R.; Gao, J.; Guo, J.; He, Y. Org. Lett. 2016, 18, 6204.
22. [22]
  Neog, K.; Dutta, D.; Das, B.; Gogoi, P. Org. Biomol. Chem. 2019, 17, 6450.
23. [23]
  Okugawa, Y.; Hayashi, Y.; Kawauchi, S.; Hirano, K.; Miura, M. Org. Lett. 2018, 20, 3670.
24. [24]
  Bhunia, A.; Kaicharla, T.; Porwal, D.; Gonnade, R. G.; Biju, A. T. Chem. Commun. 2014, 50, 11389.
25. [25]
  Bhunia, A.; Roy, T.; Gonnade, R. G.; Biju, A. T. Org. Lett. 2014, 16, 5132.
26. [26]
  Fujimoto, H.; Kusano, M.; Kodama, T.; Tobisu, M. Org. Lett. 2020, 22, 2293.
27. [27]
  Liu, Z.; Larock, R. C. J. Org. Chem. 2006, 71, 3198.
28. [28]
  Yoshida, S.; Nagai, A.; Uchida, K.; Hosoya, T. Chem. Lett. 2017, 46, 733.
29. [29]
  Pandya, V. G.; Mhaske, S. B. Org. Lett. 2014, 16, 3836.
30. [30]
  Aithagani, S. K.; Yempalla, K. R.; Munagala, G.; Vishwakarma, R. A.; Singh, P. P. RSC Adv. 2014, 4, 50208.
31. [31]
  Sumii, Y.; Sugita, Y.; Tokunaga, E.; Shibata, N. ChemistryOpen 2018, 7, 204.
32. [32]
  Zhang, L.; Li, X.; Sun, Y.; Zhao, W.; Luo, F.; Huang, X.; Lin, L.; Yang, Y.; Peng, B. Org. Biomol. Chem. 2017, 15, 7181.
33. [33]
  Sun, C.-H.; Lu, Y.; Zhang, Q.; Lu, R.; Bao, L.-Q.; Shen, M.-H.; Xu, H.-D. Org. Biomol. Chem. 2017, 15, 4058.
34. [34]
  Xu, X.-B.; Lin, Z.-H.; Liu, Y.; Guo, J.; He, Y. Org. Biomol. Chem. 2017, 15, 2716.
35. [35]
  Thangaraj, M.; Gaykar, R. N.; Roy, T.; Biju, A. T. J. Org. Chem. 2017, 82, 4470.
36. [36]
  Tan, J.; Zheng, T.; Xu, K.; Liu, C. Org. Biomol. Chem. 2017, 15, 4946.
37. [37]
  Zheng, T.; Tan, J.; Fan, R.; Su, S.; Liu, B.; Tan, C.; Xu, K. Chem. Commun. 2018, 54, 1303.
38. [38]
  Fan, R.; Liu, B.; Zheng, T.; Xu, K.; Tan, C.; Zeng, T.; Su, S.; Tan, J. Chem. Commun. 2018, 54, 7081.
39. [39]
  Jian, H.; Wang, Q.; Wang, W.-H.; Li, Z.-J.; Gu, C.-Z.; Dai, B.; He, L. Tetrahedron 2018, 74, 2876.
40. [40]
  Chen, J.; Palani, V.; Hoye, T. R. J. Am. Chem. Soc. 2016, 138, 4318.
41. [41]
  Singh, P.; Cairns, A. G.; Adolfsson, D. E.; Ådén, J.; Sauer, U. H.; Almqvist, F. Org. Lett. 2019, 21, 6946.
42. [42]
  Biswas, K. Greaney, M. F. Org. Lett. 2011, 13, 4946.
43. [43]
  Pawliczek, M.; Garve, L. K. B.; Werz, D. B. Org. Lett. 2015, 17, 1716.
44. [44]
  Li, Y.; Mük-Lichtenfeld, C.; Studer, A. Angew. Chem., Int. Ed. 2016, 55, 14435.
45. [45]
  Zhao, X.; Huang, Y.; Qing, F.-L.; Xu, X.-H. RSC Adv. 2017, 7, 47.
46. [46]
  Ahire, M. M.; Thoke, M. B.; Mhaske, S. B. Org. Lett. 2018, 20, 848.
47. [47]
  Li, Z.; Jian, H.; Wang, W.; Wang, Q.; He, L. Chin. J. Org. Chem. 2018, 38, 2045(in Chinese).
48. [48]
  Liu, Z.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 13112.
49. [49]
  Qiu, D.; He, J.; Yue, X.; Shi, J.; Li, Y. Org. Lett. 2016, 18, 3130.
50. [50]
  Gaykar, R. N.; Bhattacharjee, S.; Biju, A. T. Org. Lett. 2019, 21, 737.
51. [51]
  Yoshida, S.; Yano, T.; Misawa, Y.; Sugimura, Y.; Igawa, K.; Shimizu, S.; Tomooka, K.; Hosoya, T. J. Am. Chem. Soc. 2015, 137, 14071.
52. [52]
  Matsuzawa, T.; Uchida, K.; Yoshida, S.; Hosoya, T. Chem. Lett. 2018, 47, 825.
53. [53]
  Yoshida, S.; Nakajima, H.; Uchida, K.; Yano, T.; Kondo, M.; Matsushita, T.; Hosoya, T. Chem. Lett. 2017, 46, 77.
54. [54]
  (a) Li, H.-Y.; Xing, L.-J.; Lou, M.-M.; Wang, H.; Liu, R.-H.; Wang, B. Org. Lett. 2015, 17, 1098.
  (b) Lou, M.-M.; Wang, H.; Song, L.; Liu, H.-Y.; Li, Z.-Q.; Guo, X.-S.; Zhang, F.-G.; Wang, B. J. Org. Chem. 2016, 81, 5915.
55. [55]
  Li, Y.; Studer, A. Org. Lett. 2017, 19, 666.
56. [56]
  Li, X.; Sun, Y.; Huang, X.; Zhang, L.; Kong, L.; Peng, B. Org. Lett. 2017, 19, 838.
57. [57]
  Matsuzawa, T.; Uchida, K.; Yoshida, S.; Hosoya, T. Org. Lett. 2017, 19, 5521.
58. [58]
  Toledo, F. T.; Marques, H.; Comasseto, J. V.; Raminelli, C. Tetrahedron Lett. 2007, 48, 8125.
59. [59]
  Mesgar, M.; Daugulis, O. Org. Lett. 2017, 19, 4247.
60. [60]
  Yoshida, H.; Terayama, T.; Ohshita, J.; Kunai, A. Chem. Commun. 2004, 1980.
61. [61]
  Chen, J.; Murafuji, T. Organometallics 2011, 30, 4532.
62. [62]
  Liu, F.-L.; Chen, J.-R.; Zou, Y.-Q.; Wei, Q.; Xiao, W.-J. Org. Lett. 2014, 16, 3768.
63. [63]
  Hazarika, H.; Neog, K.; Sharma, A.; Das, B.; Gogoi, P. J. Org. Chem. 2019, 84, 5846.
64. [64]
  Li, Y.; Qiu, D.; Gu, R.; Wang, J.; Shi, J.; Li, Y. J. Am. Chem. Soc. 2016, 138, 10814.
65. [65]
  Lin, W.; Sapountzis, I.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 4258.
66. [66]
  García-López, J.-A.; Çetin, M.; Greaney, M. F. Angew. Chem., Int. Ed. 2015, 54, 2156.
67. [67]
  Zeng, Y.; Hu, J. Org. Lett. 2016, 18, 856.
68. [68]
  Peng, X.; Ma, C.; Tung, C.-H.; Xu, Z. Org. Lett. 2016, 18, 4154.
69. [69]
  Kwon, J.; Kim, B. M. Org. Lett. 2019, 21, 428.
70. [70]
  Gaykar, R. N.; Guin, A.; Bhattacharjee, S.; Biju, A. T. Org. Lett. 2019, 21, 9613.
71. [71]
  Zhao, J.; Larock, R. C. J. Org. Chem. 2007, 72, 583.
72. [72]
  Hall, C.; Henderson, J. L.; Ernouf, G.; Greaney, M. F. Chem. Commun. 2013, 49, 7602.
73. [73]
  Shi, J.; Qiu, D.; Wang, J.; Xu, H.; Li, Y. J. Am. Chem. Soc. 2015, 137, 5670.
74. [74]
  Palani, V.; Chen, J.; Hoye, T. R. Org. Lett. 2016, 18, 6312.
75. [75]
  Chen, Y.; Willis, M. C. Org. Lett. 2015, 17, 4786.
76. [76]
  Pawliczek, M.; Garve, L. K. B.; Werz, D. B. Chem. Commun. 2015, 51, 9165.
77. [77]
  Garg, P.; Singh, A. Org. Lett. 2018, 20, 1320.
78. [78]
  Ding, W.; Yu, A.; Zhang, L.; Meng, X. Org. Lett. 2019, 21, 9014.
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