Citation: Du Jianbo, Chen Yuegang, Zuo Zhiwei. Recent Progress of Photocatalytic Methylation of Arenes[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3646-3655. doi: 10.6023/cjoc202006079 shu

Recent Progress of Photocatalytic Methylation of Arenes

Du Jianbo ^a ,
Chen Yuegang ^a ,
Zuo Zhiwei ^a,b,,

a.
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Zuo Zhiwei, zuozhw@sioc.ac.cn
Received Date: 30 June 2020
Revised Date: 7 August 2020
Available Online: 17 August 2020
Fund Project: National Natural Science Foundation of China 21971163National Natural Science Foundation of China 21772121Project supported by the National Natural Science Foundation of China (Nos. 21772121, 21971163)

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Methylation of arenes is one of the versatile approaches to achieve structural modification in organic and medicinal chemistry. Installation of a methyl group onto an aromatic ring can lead to significant improvenent of the physical properties and biological activity of this molecule, thusly the effect oftentimes is called the"magic methyl effect". During the past few years, visible-light-induced photocatalysis has emerged as a powerful tool for the development of efficient transformations in organic synthesis. Compared to traditional radical mediated reactions, the use of visible light as energy input is more environmentally benign. Recently, a series of aryl methylation reactions enabled by visible light photoredox catalysis have been reported and applied in the synthesis of pharmaceutically-interested products. In this review, the recent progress of visible-light-induced aryl methylation reactions is briefly summaried, with discussions of different reaction pathways.
- methylation,
- radical-mediated reaction,
- methyl radical,
- photoredox catalysis
1. [1]
  (a) Friesen, R. W.; Brideau, C.; Chan, C. C.; Charleson, S.; Deschanes, D.; Dub, D.; Ethier, D.; Fortin, R.; Gauthier, J. Y.; Girard, Y.; Gordon, R.; Greig, G. M.; Riendeau, D.; Savoie, C.; Wang, Z.; Wong, E.; Visco, D.; Xu, L.-J.; Young, R. N. Bioorg. Med. Chem. Lett. 1998, 8, 2777.
  (b) Li, L.; Beaulieu, C.; Carriere, M. C.; Denis, D.; Greig, G.; Guay, D.; ONeill, G.; Zamboni, R.; Wang. Z. Bioorg. Med. Chem. Lett. 2010, 20, 7462.
  (c) Ginnings, P. M.; Baum. R. J. Am. Chem. Soc. 1937, 59, 1111.
2. [2]
  Schönherr, H.; Cernak, T. Angew. Chem., Int. Ed. 2013, 52, 12256. doi: 10.1002/anie.201303207
3. [3]
  (a) McGrath, N. A.; Brichacek, M.; Njardarson, J. T. J. Chem. Educ. 2010, 87, 1348.
  (b) Barreiro, E. J.; Kmmerle, A. E.; Fraga, C. A. M. Chem. Rev. 2011, 111, 5215.
4. [4]
  (a) Potthast, A.; Rosenau, T.; Chen, C.-L.; Gratzl, J. S. J. Org. Chem. 1995, 60, 4320.
  (b) Friedman, L.; Fishel, D. L.; Shechter, H. J. Org. Chem. 1965, 30, 1453.
  (c) Friedman, L. Org. Synth. 1963, 43, 80.
  (d) Das, S.; Bhowmick, T.; Punnyamurthy, T.; Dey, D.; Nath, J.; Chaudhuri, M. K. Tetrahedron Lett. 2003, 44, 4915.
  (e) Shimada, K.; Nanae, T.; Aoyagi, S.; Takikawa, Y.; Kabuto, C. Tetrahedron Lett. 2001, 42, 6167.
5. [5]
  (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
  (b) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
  (c) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236.
  (d) Yan, G.-B.; Borah, A. J.; Wang, L.-G.; Yang, M.-H. Adv. Synth. Catal. 2015, 357, 1333.
  (e) Chen, Y.-T. Chem.-Eur. J. 2019, 25, 3405.
  (f) Hu, L.; Liu, Y.-A.; Liao, X. Synlett 2018, 29, 375.
  (g) Feng, K.; Quevedo, R. E.; Kohrt, J. T.; Oderinde, M. S.; Reilly, U.; White, M. C. Nature 2020, 580, 621.
  (h) Feng, B.; Yang, Y.; You, J. Chem. Sci. 2020, 11, 6031.
  (i) Chen, X.-Y.; Sorensen, E. J. J. Am. Chem. Soc. 2018, 140, 2789.
  (j) He, Z.-T.; Li, H.; Haydl, A.; Whiteker, G.; Hartwig, J. F. J. Am. Chem. Soc. 2018, 140, 17197.
  (k) Serpier, F.; Pan, F.; Ham, W. S.; Jacq, J.; Genicot, C.; Ritter, T. Angew. Chem., Int. Ed. 2018, 57, 10697.
  (l) Lv, W.; Wen, S.; Liu, J.; Cheng, G. J. Org. Chem. 2019, 84, 9786.
6. [6]
  (a) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102.
  (b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
  (c) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176.
  (d) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
  (e) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828.
  (f) Chen, Y.; Lu, L.-Q.; Yu, D.-G.; Zhu, C.-J.; Xiao, W.-J. Sci. China: Chem. 2019, 62, 24.
7. [7]
  (a) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299.
  (b) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525.
  (c) Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656.
8. [8]
  ana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417. doi: 10.1021/cr100327p
9. [9]
  Zhang, P.; Le, C. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2016, 138, 8084. doi: 10.1021/jacs.6b04818
10. [10]
  Biswas, S.; Weix, D. J. J. Am. Chem. Soc. 2013, 135, 16192. doi: 10.1021/ja407589e
11. [11]
  Kariofillis, S. K.; Shields, B. J.; Tekle-Smith, M. A.; Zacuto, M. J.; Doyle, A. G. J. Am. Chem. Soc. 2013, 135, 16192. doi: 10.1021/ja407589e
12. [12]
  Sato, Y.; Nakamura, K.; Sumida, Y.; Hashizume, D.; Hosoya, T.; Ohmiya, H. J. Am. Chem. Soc. 2020, 142, 9938. doi: 10.1021/jacs.0c04456
13. [13]
  Schuster, G. B. Pure Appl. Chem. 1990, 62, 156.
14. [14]
  (a) Minisci, F.; Bernardi, R.; Bertini, F.; Galli, R.; Perchinummo, M. Tetrahedron 1971, 27, 3575.
  (b) Proctor, R. S.; Phipps, R. J. Angew. Chem., Int. Ed. 2019, 58, 13666.
15. [15]
  DiRocco, D. A.; Dykstra, K.; Krska, S.; Vachal, P.; Conway, D. V.; Tudge, M. Angew. Chem., Int. Ed. 2014, 53, 4802. doi: 10.1002/anie.201402023
16. [16]
  Komai, T.; Matsuyama, K.; Matsushima, M. Bull. Chem. Soc. Jpn. 1988, 61, 1641. doi: 10.1246/bcsj.61.1641
17. [17]
  MorletSavary, F.; Wieder, F.; Fouassier, J. P. J. Chem. Soc. Faraday Trans. 1997, 93, 3931. doi: 10.1039/a704951j
18. [18]
  Tarantino, K. T.; Liu, P.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 10022. doi: 10.1021/ja404342j
19. [19]
  Jin, J.; MacMillan, D. W. C. Nature 2015, 525, 87. doi: 10.1038/nature14885
20. [20]
  Wessig, P.; Muehling, O. Eur. J. Org. Chem. 2007, 2219.
21. [21]
  Li, G.-X.; Christian A.; Rivera, M.; Wang, Y.-X.; Gao, F.; He, G.; Liu, P.; Chen, G. Chem. Sci. 2016, 7, 6407. doi: 10.1039/C6SC02653B
22. [22]
  (a) Huang, H.; Jia, K.; Chen, Y. Angew. Chem., Int. Ed. 2015, 54, 1881.
  (b) Huang, H.; Zhang, G.; Gong, L.; Zhang, S.; Chen, Y. J. Am. Chem. Soc. 2014, 136, 2280.
  (c) Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433.
  (d) Khatib, M. E.; Seraphim, R. A. M.; Molander, G. A. Angew. Chem., Int. Ed. 2016, 55, 254.
23. [23]
  Zhang, W.-M.; Dai, J.-J.; Xu, J.; Xu, H.-J. J. Org. Chem. 2017, 82, 2059. doi: 10.1021/acs.joc.6b02891
24. [24]
  Liu, W.-B.; Yang, X.-B.; Zhou, Z.-Z.; Li, C.-J. Chemistry 2017, 2, 688. doi: 10.1016/j.chempr.2017.03.009
25. [25]
  Sherwood, T. C.; Li, N.; Yazdani, A. N.; Dhar, T. G. M. J. Org. Chem. 2018, 83, 3000. doi: 10.1021/acs.joc.8b00205
26. [26]
  Garza-Sanchez, R. A.; Patra, T.; Tlahuext-Aca, A.; Strieth-Kalthoff, F.; Glorius, F. Chem.-Eur. J. 2018, 24, 10064. doi: 10.1002/chem.201802352
27. [27]
  Hu, A.-H.; Guo, J.-J.; Pan, H.; Zuo, Z.-W. Science 2018, 361, 668. doi: 10.1126/science.aat9750
28. [28]
  Zidan, M.; Morris, A. O.; McCallum, T.; Barriault, L. Eur. J. Org. Chem. 2020, 1453.
29. [29]
  Li, Z.-L.; Wang, X.-F.; Xia, S.-Q.; Jin, J. Org. Lett. 2019, 21, 4259. doi: 10.1021/acs.orglett.9b01439
30. [30]
  Le, C.; Liang, Y.-F.; Evans, R. W.; Li, X.-M.; MacMillan, D. W. C. Nature 2017, 547, 79. doi: 10.1038/nature22813
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