Recent Advances in Visible-Light-Catalyzed C—C Bonds and C—Heteroatom Bonds Formation Using Sulfonium Salts

doi:10.6023/cjoc202209004

Abstract

Sulfonium salts are one of the most important class of organosulfur (IV) compounds which have a positive charge on the sulfur center with three C—S bonds. Because of their bench-stable, easy synthesis, broad structural diversity, and rich reactivity, sulfonium salts are playing a significant role in synthetic chemistry. In recent years, visible-light promoted photoredox catalysis is rapidly developing into a powerful tool for organic synthesis. In this paper, the recent advances of different sulfonium salts in the radical type reactions induced by visible light are summarized. The formation reactions of C—C bond and C—X (X=B, N, O, S, Se, Te, F, Cl, I) bonds are introduced, and the applicable scope and mechanism of some reactions are also discussed.

Key words: sulfur chemistry, sulfonium salt, visible light, free radical reaction

Cite this article

Hao Xu, Jie Zhang, Junze Zuo, Fengxiao Wang, Jian Lü, Xu Hun, Daoshan Yang. Recent Advances in Visible-Light-Catalyzed C—C Bonds and C—Heteroatom Bonds Formation Using Sulfonium Salts[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4037-4059.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 34

Scheme 1. Conventional methods for the synthesis of sulfonium salts

Scheme 2. Reaction mode of sulfonium salts

Scheme 3. Radical type reactions involving sulfonium salts

Scheme 4. Light induced desulphurization of sulfonium salts leading to acetophenone

Scheme 5. Visible-light-promoted approach to 6-trifluoroethyl phenanthridines using Umemoto’s reagent as the CF3 source

Scheme 6. Visible-light-induced perylene-catalyzed aminodifluoromethylation of alkenes

Scheme 7. Visible light-induced aryltrifluoromethylation of hydroxy alkenes

Scheme 8. Metallaphotoredox-catalysed radical alkylation of benzylsulfonium salts

Scheme 9. Photoredox-catalysed radical alkylation of sulfonium salts

Scheme 10. Visible-light-promoted desulfurative alkylation of alkyl thianthrenium salts with activated olefins

Scheme 11. Visible-light-driven photoredox-catalyzed and copper(II)-assisted three-component approach to γ-hydroxy carbonyl compounds

Scheme 12. Visible-light photocatalytic reduction of sulfonium salts as a source of aryl radicals

Scheme 13. Visible-light-promoted trifluoromethylation of isonitrile and olefins

Scheme 14. Photoredox-catalyzed alkenylation of benzylsulfoniums

Scheme 15. Alkylsulfonium salts for photochemical desulphurizative functionalization of heteroarenes

Scheme 16. Indirect cyanidation of derivatives of insecticide pyrrolyl ether

Scheme 17. Photoinduced copper-catalyzed site-selective C(sp2)—C(sp) cross-coupling via aryl sulfonium salts

Scheme 18. Synthesis of alkynylated pyrrole derivatives by photocatalysis

Scheme 19. Copper-catalyzed cross-coupling reactions using alkyl thianthrenium salts

Scheme 20. Desulphurization strategy for Sonogashira couplings by visible light/copper catalysis

Scheme 21. Metal-free photoredox-catalyzed formal C—H/C—H coupling of arenes

Scheme 22. Arylation of ortho-Hydroxyarylenaminones by Sulfonium Salts

Scheme 23. Photocatalytic arylation of aryl sulfonium salts

Scheme 24. Palladium metallaphotoredox-catalyzed 2?arylation of indole derivatives

Scheme 25. Ritter’s pioneering work on C—H functionalization of aromatic compounds

Scheme 26. Site-selective C—H oxygenation via aryl sulfonium salts

Scheme 27. Ritter’s work on building C-heteroatom bonds using aryl sulfonium salts

Scheme 28. Employing alkynyl sulfonium salts as chalcogen-bonding catalysts

Scheme 29. Borylation of aryl sulfonium salts via C—S activation enabled by light

Scheme 30. Generation of non-stabilized alkyl radicals from thianthrenium salts for C—B bond formation

Scheme 31. Visible-light-initiatede trifluoromethylselenolation of arylsulfonium salts with [Me4N][SeCF3]

Scheme 32. Visible-light catalyzed reaction of thianthrenium salts, sulfur dioxide and hydrazines

Scheme 33. Photoredox-catalyzed α?sulfonylation of ketones from sulfur dioxide and thianthrenium salts

Scheme 34. Radical type ring opening of sulfonium salts with dichalcogenides by visible light and copper catalysis

References 43

[1]	(a) Kozhushkov, S. I.; Alcarazo, M. Eur. J. Inorg. Chem. 2020, 2486.
	(b) Wang, M.; Jiang, X. ACS Sustainable Chem. Eng. 2022, 10, 671. doi: 10.1021/acssuschemeng.1c07636
	(c) Gan, Z.; Zhu, X.; Yan, Q.; Song, X.; Yang, D. Chin. Chem. Lett. 2021, 32, 1705. doi: 10.1016/j.cclet.2020.12.046
[2]	Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832. doi: 10.1021/jm401375q
[3]	(a) Mondal, M.; Chen, S.; Kerrigan, N. J. Molecules 2018, 23, 738. doi: 10.3390/molecules23040738
	(b) Nenaidenko, V. G.; Balenkova, E. S. Russ. J. Org. Chem. 2003, 39, 291. doi: 10.1023/A:1025525327399
	(c) Chen, J.; Li, J.; Plutschack, M. B.; Berger, F.; Ritter, T. Angew. Chem., Int. Ed. 2020, 59, 5616 doi: 10.1002/anie.201914215
	(d) Chen, X.-Y.; Huang, Y.-H.; Zhou, J.; Wang, P. Chin. J. Chem. 2020, 38, 1269 doi: 10.1002/cjoc.202000212
	(e) Nie, X.-X.; Huang, Y.-H.; Wang, P. Org. Lett. 2020, 22, 7716. doi: 10.1021/acs.orglett.0c02913
	(f) Kendall, A. J.; Mock, M. T. Eur. J. Inorg. Chem. 2020, 1347.
	(g) Tian, Z.-Y.; Hu, Y.-T.; Teng, H.-B.; Zhang, C.-P. Tetrahedron Lett. 2018, 59, 299. doi: 10.1016/j.tetlet.2017.12.005
	(h) Chen, J.; Li, J.; Plutschack, M. B.; Berger, F.; Ritter, T. Angew. Chem., Int. Ed. 2020, 59, 5616. doi: 10.1002/anie.201914215
	(i) Kendall, A. J.; Mock, M. T. Eur. J. Inorg. Chem. 2020, 1347.
	(j) Tian, Z.-Y.; Ma, Y.; Zhang, C.-P. Synthesis 2022, 54, 1478. doi: 10.1055/a-1677-5971
	(k) Wang, C.; Liu, B.; Shao, Z.; Zhou, J.; Shao, A.; Zou, L.-H.; Wen, J. Org. Lett. 2022, 24, 5391. doi: 10.1021/acs.orglett.2c02078
[4]	(a) Kaiser, D.; Klose, I.; Oost, R.; Neuhaus, J.; Maulide, N. Chem. Rev. 2019, 119, 8701. doi: 10.1021/acs.chemrev.9b00111
	(b) Kozhushkov, S. I.; Alcarazo, M. Eur. J. Inorg. Chem. 2020, 2486.
	(c) Péter, Á.; Perry, G. J. P.; Procter, D. J. Adv. Synth. Catal. 2020, 362, 2135. doi: 10.1002/adsc.202000220
	(d) Yorimitsu, H. Chem. Rec. 2021, 21, 3356. doi: 10.1002/tcr.202000172
	(e) Tian, J.; Gao, W. C.; Jiang, X.-F. Chem. Reagents 2021, 43, 447. (in Chinese)
	( 田俊, 高文超, 姜雪峰, 化学试剂, 2021, 43, 447.)
[5]	Broderick, J. B.; Duffus, B. R.; Duschene, K. S.; Shepard, E. M. Chem. Rev. 2014, 114, 4229. doi: 10.1021/cr4004709 pmid: 24476342
[6]	(a) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611. doi: 10.1021/ar030045f
	(b) Lu, L.-Q.; Li, T.-R.; Wang, Q.; Xiao, W.-J. Chem. Soc. Rev. 2017, 46, 4135. doi: 10.1039/C6CS00276E
	(c) Shi, J.; Li, Y.; Li, Y. Chem. Soc. Rev. 2017, 46, 1707. doi: 10.1039/C6CS00694A
[7]	Garst, M. E.; McBride, B. J.; Johnson, A. T. J. Org. Chem. 1983, 48, 8. doi: 10.1021/jo00149a003
[8]	Wang, L.; He, W.; Yu, Z. Chem. Soc. Rev. 2013, 42, 599. doi: 10.1039/C2CS35323G
[9]	Otsuka, S.; Nogi, K.; Yorimitsu, H. Top. Curr. Chem. 2018, 376, 13.
[10]	(a) Beeson, T. D.; Mastracchio, A.; Hong, J.-B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582. doi: 10.1126/science.1142696
	(b) Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2009, 131, 14604. doi: 10.1021/ja903732v
	(c) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176. doi: 10.1126/science.1239176
[11]	(a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r pmid: 28762417
	(b) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Acc. Chem. Res. 2016, 49, 1911 doi: 10.1021/acs.accounts.6b00254 pmid: 28762417
	(c) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075. doi: 10.1021/acs.chemrev.6b00057 pmid: 28762417
	(d) Xie, L.-Y.; Peng, S.; Yang, L.-H.; Peng, C.; Lin, Y.-W.; Yu, X.; Cao, Z.; Peng, Y.-Y.; He, W.-M. Green Chem. 2021, 23, 374. doi: 10.1039/D0GC02844D pmid: 28762417
	(e) Liu, Y.; Chen, X.-L.; Li, X.-Y.; Zhu, S.-S.; Li, S.-J.; Song, Y.; Qu, L.-B.; Yu, B. J. Am. Chem. Soc. 2021, 143, 964. doi: 10.1021/jacs.0c11138 pmid: 28762417
	(f) Li, G.-H.; Han, Q.-Q.; Sun, Y.-Y.; Chen, D.-M.; Wang, Z.-L.; Xu, X.-M.; Yu, X.-Y. Chin. Chem. Lett. 2020, 31, 3255. doi: 10.1016/j.cclet.2020.03.007 pmid: 28762417
	(g) Wang, Z.; Liu, Q.; Ji, X.; Deng, G.-J.; Huang, H. ACS Catal. 2020, 10, 154. doi: 10.1021/acscatal.9b04411 pmid: 28762417
	(h) Kim, J.; Kim, D.; Chang, S. J. Am. Chem. Soc. 2020, 142, 19052. doi: 10.1021/jacs.0c09982 pmid: 28762417
	(i) Zhang, Q.-B.; Ban, Y.-L.; Zhou, D.-G.; Zhou, P.-P.; Wu, L.-Z.; Liu, Q. Org. Lett. 2016, 18, 5256. doi: 10.1021/acs.orglett.6b02560 pmid: 28762417
	(j) Wu, C.; Bian, Q.; Ding, T.; Tang, M.; Zhang, W.; Xu, Y.; Liu, B.; Xu, H.; Li, H.-B.; Fu, H. ACS Catal. 2021, 11, 9561. doi: 10.1021/acscatal.1c02272 pmid: 28762417
	(k) He, S.; Chen, X.; Zeng, F.; Lu, P.; Peng, Y.; Qu, L.; Yu, B. Chin. Chem. Lett. 2020, 31, 1863. doi: 10.1016/j.cclet.2019.12.031 pmid: 28762417
	(l) Yang, D.; Yan, Q.; Zhu, E.; Lv, J.; He, W.-M. Chin. Chem. Lett. 2022, 33, 1798. doi: 10.1016/j.cclet.2021.09.068 pmid: 28762417
	(m) Meng, N.; Lv, Y.; Liu, Q.; Liu, R.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2021, 32, 258. doi: 10.1016/j.cclet.2020.11.034 pmid: 28762417
	(n) Meng, Q.-Y.; Schirmer, T. E.; Berger, A. L.; Donabauer, K.; König, B. J. Am. Chem. Soc. 2019, 141, 11393. doi: 10.1021/jacs.9b05360 pmid: 28762417
	(o) Bagdi, A. K.; Rahman, M.; Bhattacherjee, D.; Zyryanov, G. V.; Ghosh, S.; Chupakhin, O. N.; Hajra, A. Green Chem. 2020, 22, 6632. doi: 10.1039/D0GC02437F pmid: 28762417
	(p) Fu, Q.; Bo, Z.-Y.; Ye, J.-H.; Ju, T.; Huang, H.; Liao, L.-L.; Yu, D.-G. Nat. Commun. 2019, 10, 3592. doi: 10.1038/s41467-019-11528-8 pmid: 28762417
	(q) Xie, J.; Jin, H.; Hashmi, A. S. K. Chem. Soc. Rev. 2017, 46, 5193. doi: 10.1039/c7cs00339k pmid: 28762417
	(r) Chen, B.; Wu, L.-Z.; Tung, C.-H. Acc. Chem. Res. 2018, 51, 2512. doi: 10.1021/acs.accounts.8b00267 pmid: 28762417
[12]	Speckmeier, E.; Fischer, T. G.; Zeitler, K. J. Am. Chem. Soc. 2018, 140, 15353. doi: 10.1021/jacs.8b08933 pmid: 30277767
[13]	Tam, W. J. Am. Chem. Soc. 2002, 124, 12630.
[14]	Hu, J.; Zhu, Z.; Xie, Z.; Le, Z. Chin. J. Org. Chem. 2022, 42, 978. (in Chinese) doi: 10.6023/cjoc202110020
	( 胡家榆, 祝志强, 谢宗波, 乐长高, 有机化学, 2022, 42, 978.) doi: 10.6023/cjoc202110020
[15]	Hedstrand, D. M.; Kruizinga, W. H.; Kellogg, R. M. Tetrahedron Lett. 1978, 19, 1255. doi: 10.1016/S0040-4039(01)94515-0
[16]	Sun, X.; Yu, S. Chem. Commun. 2016, 52, 10898. doi: 10.1039/C6CC05756J
[17]	Noto, N.; Koike, T.; Akita, M. Chem. Sci. 2017, 8, 6375. doi: 10.1039/C7SC01703K
[18]	Wang, H.; Xu, Q.; Yu, S. Org. Chem. Front. 2018, 5, 2224. doi: 10.1039/C8QO00430G
[19]	Varga, B.; Gonda, Z.; Tóth, B. L.; Kotschy, A.; Novák, Z. Eur. J. Inorg. Chem. 2020, 2020, 1466. doi: 10.1002/ejoc.201900957
[20]	Chen, C.; Wang, Z.-J.; Lu, H.; Zhao, Y.; Shi, Z. Nat. Commun. 2021, 12, 4526. doi: 10.1038/s41467-021-24716-2
[21]	Li, X.; Si, W.; Liu, Z.; Qian, H.; Wang, T.; Leng, S.; Sun, J.; Jiao, Y.; Zhang, X. Org. Lett. 2022, 24, 4070. doi: 10.1021/acs.orglett.2c01525
[22]	Yan, D.-M.; Xu, S.-H.; Qian, H.; Gao, P.-P.; Bi, M.-H.; Xiao, W.-J.; Chen, J.-R. ACS Catal. 2022, 12, 3279. doi: 10.1021/acscatal.2c00638
[23]	Donck, S.; Baroudi, A.; Fensterbank, L.; Goddard, J.-P.; Ollivier, C. Adv. Synth. Catal. 2013, 355, 1477. doi: 10.1002/adsc.201300040
[24]	(a) Cheng, Y.; Yuan, X.; Jiang, H.; Wang, R.; Ma, J.; Zhang, Y.; Yu, S. Adv. Synth. Catal. 2014, 356, 2859. doi: 10.1002/adsc.201400504
	(b) Wang, H.; Cheng, Y.; Yu, S. Sci. China: Chem. 2016, 59, 195.
	(c) Yu, S.; Zhang, Y.; Wang, R.; Jiang, H.; Cheng, Y.; Kadi, A.; Fun, H.-K. Synthesis 2014, 46, 2711. doi: 10.1055/s-0034-1379217
[25]	Otsuka, S.; Nogi, K.; Rovis, T.; Yorimitsu, H. Chem. Asian. J. 2019, 14, 532. doi: 10.1002/asia.201801732
[26]	Zhu, X.; Jiang, M.; Li, X.; Zhu, E.; Deng, Q.; Song, X.; Lv, J.; Yang, D. Org. Chem. Front. 2022, 9, 347. doi: 10.1039/D1QO01570B
[27]	(a) Berger, F.; Plutschack, M. B.; Riegger, J.; Yu, W.; Speicher, S.; Ho, M.; Frank, N.; Ritter, T. Nature 2019, 567, 223. doi: 10.1038/s41586-019-0982-0
	(b) Ritter, T.; Berger, F. Synlett 2021, 33, 339. doi: 10.1055/s-0040-1706034
	(c) Sang, R.; Korkis, S. E.; Su, W.; Ye, F.; Engl, P. S.; Berger, F.; Ritter, T. Angew. Chem., Int. Ed. 2019, 58, 16161. doi: 10.1002/anie.201908718
[28]	Liang, L.; Niu, H. Y.; Li, R. L.; Wang, Y. F.; Yan, J. K.; Li, C. G.; Guo, H. M. Org. Lett. 2020, 22, 6842. doi: 10.1021/acs.orglett.0c02364 pmid: 32810404
[29]	Lu, Y.; Liu, Q.; Wang, Z.-X.; Chen, X.-Y. Angew. Chem., Int. Ed. 2022, 61, e202116071.
[30]	Li, X.; Jiang, M.; Zhu, X.; Song, X.; Deng, Q.; Lv, J.; Yang, D. Org. Chem. Front. 2022, 9, 386. doi: 10.1039/D1QO01548F
[31]	Aukland, M. H.; Šiaučiulis, M.; West, A.; Perry, G. J. P.; Procter, D. J. Nat. Catal. 2020, 3, 163. doi: 10.1038/s41929-019-0415-3
[32]	Mkrtchyan, S.; Iaroshenko, V. O. J. Org. Chem. 2021, 86, 4896. doi: 10.1021/acs.joc.0c02294
[33]	Sun, K.; Shi, A.; Liu, Y.; Chen, X.; Xiang, P.; Wang, X.; Qu, L.; Yu, B. Chem. Sci. 2022, 13, 5659. doi: 10.1039/D2SC01241C
[34]	Wang, X.; Xun, X.; Song, H.; Liu, Y.; Wang, Q. Org. Lett. 2022, 24, 4580. doi: 10.1021/acs.orglett.2c01674
[35]	Engl, P. S.; Haring, A. P.; Berger, F.; Berger, G.; Perez-Bitrian, A.; Ritter, T. J. Am. Chem. Soc. 2019, 141, 13346. doi: 10.1021/jacs.9b07323
[36]	Ye, F.; Berger, F.; Jia, H.; Ford, J.; Wortman, A.; Borgel, J.; Genicot, C.; Ritter, T. Angew. Chem., Int. Ed. 2019, 58, 14615. doi: 10.1002/anie.201906672
[37]	Li, J.; Chen, J.; Sang, R.; Ham, W. S.; Plutschack, M. B.; Berger, F.; Chabbra, S.; Schnegg, A.; Genicot, C.; Ritter, T. Nat. Chem. 2020, 12, 56. doi: 10.1038/s41557-019-0353-3
[38]	Huang, C.; Feng, J.; Ma, R.; Fang, S.; Lu, T.; Tang, W.; Du, D.; Gao, J. Org. Lett. 2019, 21, 9688. doi: 10.1021/acs.orglett.9b03850 pmid: 31755274
[39]	Chen, C.; Wang, Z. J.; Lu, H.; Zhao, Y.; Shi, Z. Nat. Commun. 2021, 12, 4526. doi: 10.1038/s41467-021-24716-2
[40]	Tian, Z.-Y.; Zhang, C.-P. Org. Chem. Front. 2022, 9, 2220. doi: 10.1039/D2QO00235C
[41]	Li, Q.; Huang, J.; Cao, Z.; Zhang, J.; Wu, J. Org. Chem. Front. 2022, 9, 3781. doi: 10.1039/D2QO00768A
[42]	He, F.-S.; Bao, P.; Tang, Z.; Yu, F.; Deng, W.-P.; Wu, J. Org. Lett. 2022, 24, 2955. doi: 10.1021/acs.orglett.2c01132
[43]	Cui, W.; Li, X.; Guo, G.; Song, X.; Lv, J.; Yang, D. Org. Lett. 2022, 24, 5391. doi: 10.1021/acs.orglett.2c02078

硫鎓盐在可见光催化构建C—C键及C—杂原子键中的应用进展