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.
1. [1]
  Wen Jiang , Jieli Lin , Zhongshu Li . 低配位含磷官能团的研究进展. University Chemistry, 2025, 40(8): 138-151. doi: 10.12461/PKU.DXHX202409144
2. [2]
  Junyuan Zhang , Zhiwei Miao . 有机磷杀虫剂的前世今生. University Chemistry, 2025, 40(6): 129-138. doi: 10.12461/PKU.DXHX202408118
3. [3]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
4. [4]
  Fengxiao Wang , Zhiwei Miao , Yaofeng Yuan . 有机磷化学与化学教学. University Chemistry, 2025, 40(8): 158-168. doi: 10.12461/PKU.DXHX202410077
5. [5]
  Qilong Fang , Yiqi Li , Jiangyihui Sheng , Quan Yuan , Jie Tan . Magical Pesticide Residue Detection Test Strips: Aptamer-based Lateral Flow Test Strips for Organophosphorus Pesticide Detection. University Chemistry, 2024, 39(5): 80-89. doi: 10.3866/PKU.DXHX202310004
6. [6]
  Shuai Yuan , Yaofeng Yuan . Academician Chengye Yuan and Organic Phosphorus Chemistry. University Chemistry, 2025, 40(7): 393-400. doi: 10.12461/PKU.DXHX202409123
7. [7]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
8. [8]
  Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
9. [9]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
10. [10]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
11. [11]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
12. [12]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
13. [13]
  Hong CAI , Jiewen WU , Jingyun LI , Lixian CHEN , Siqi XIAO , Dan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382
14. [14]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
15. [15]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086
16. [16]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
17. [17]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
18. [18]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
19. [19]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
20. [20]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036

Get Citation

PDF

XML

Metrics

PDF Downloads(137)
Abstract views(6178)
HTML views(1267)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142