Synthesis 2021; 53(19): 3440-3468
DOI: 10.1055/a-1509-5541
review

Visible Light as the Key for the Formation of Carbon–Sulfur Bonds in Sulfones, Thioethers, and Sulfonamides: An Update

Emanuele Azzi
,
Alberto Lanfranco
,
Riccardo Moro
,
Annamaria Deagostino
,
This work was supported by MIUR (Ministero Italiano dell’Università e della Ricerca).


Abstract

This review summarizes the most relevant advancements made in the photocatalyzed synthesis of sulfones, thioethers, and sulfonamides from 2017 to the beginning of 2021. Synthetic strategies towards the construction of sulfur–carbon bonds are discussed together with the proposed reaction mechanisms. Interestingly, sulfur-based functional groups, which are of fundamental importance for the pharmaceutical field, can be assembled by photocatalysis in an easy and straightforward way under milder reaction conditions employing less toxic and expensive sulfur sources in comparison with common strategies.

1 Introduction

2 Sulfones

2.1 Sodium Sulfinates and Sulfinic Acids

2.2 Sulfonyl Halides

2.3 Sulfonyl Hydrazones

2.4 Sulfur Dioxide Surrogates

2.5 Miscellaneous

3 Thioethers

4 Sulfonamides

5 Conclusions



Publication History

Received: 12 May 2021

Accepted: 17 May 2021

Accepted Manuscript online:
17 May 2021

Article published online:
07 July 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Feng M, Tang B, Liang SH, Jiang X. Curr. Top. Med. Chem. 2016; 16: 1200
    • 1b Zhu H, Dronamraju V, Xie W, More SS. Med. Chem. Res. 2021; 30: 305
    • 1c Majumdar KC, Mondal S. Chem. Rev. 2011; 111: 7749
  • 2 Scott KA, Njardarson JT. Top. Curr. Chem. 2018; 376: 5
    • 3a Zhao C, Rakesh KP, Ravidar L, Fang W.-Y, Qin H.-L. Eur. J. Med. Chem. 2019; 162: 679
    • 3b Jacob C. Nat. Prod. Rep. 2006; 23: 851
    • 4a Zhu J, Yang W.-C, Wang X.-d, Wu L. Adv. Synth. Catal. 2018; 360: 386
    • 4b Qiu G, Zhou K, Gao L, Wu J. Org. Chem. Front. 2018; 5: 691
    • 4c Ye S, Li X, Xie W, Wu J. Eur. J. Org. Chem. 2020; 1274
  • 5 Wimmer A, König B. Beilstein J. Org. Chem. 2018; 14: 54
  • 6 Meyer AU, Jäger S, Prasad Hari D, König B. Adv. Synth. Catal. 2015; 357: 2050
  • 7 Meyer AU, Straková K, Slanina T, König B. Chem. Eur. J. 2016; 22: 8694
  • 8 Meyer AU, Lau VW.-h, König B, Lotsch BV. Eur. J. Org. Chem. 2017; 2179
  • 9 Sun D, Zhang R. Org. Chem. Front. 2018; 5: 92
  • 10 Wang J.-J, Yu W. Org. Lett. 2019; 21: 9236
  • 11 Zheng Y, You Y, Shen Q, Zhang J, Liu L, Duan X.-H. Org. Chem. Front. 2020; 7: 2069
  • 12 Huang HM, Bellotti P, Pflüger PM, Schwarz JL, Heidrich B, Glorius F. J. Am. Chem. Soc. 2020; 142: 10173
  • 13 Bellotti P, Koy M, Gutheil C, Heuvel S, Glorius F. Chem. Sci. 2021; 12: 1810
  • 14 Yuan J.-M, Li J, Zhou H, Xu J, Zhu F, Liang Q, Liu Z, Huang G, Huang J. New J. Chem. 2020; 44: 3189
  • 15 Johnson TC, Elbert BL, Farley AJ. M, Gorman TW, Genicot C, Lallemand B, Pasau P, Flasz J, Castro JL, Maccoss M, Dixon DJ, Paton RS, Schofield CJ, Smith MD, Willis MC. Chem. Sci. 2018; 9: 629
  • 16 Yue H, Zhu C, Rueping M. Angew. Chem. Int. Ed. 2018; 57: 1371
  • 17 Liu N.-W, Hofman K, Herbert A, Manolikakes G. Org. Lett. 2018; 20: 760
  • 18 Cabrera-Afonso MJ, Lu Z.-P, Kelly CB, Lang SB, Dykstra R, Gutierrez O, Molander GA. Chem. Sci. 2018; 9: 3186
  • 19 Zhu D.-L, Wu Q, Li H.-Y, Li H.-X, Lang J.-P. Chem. Eur. J. 2020; 26: 3484
  • 20 Chawla R, Yadav LD. S. Org. Biomol. Chem. 2019; 17: 4761
  • 21 Li P, Wang GW. Org. Biomol. Chem. 2019; 17: 5578
  • 22 He J, Chen G, Zhang B, Li Y, Chen J.-R, Xiao W.-J, Liu F, Li C. Chem 2020; 6: 1149
  • 23 Griesser M, Chauvin J.-PR, Pratt DA. Chem. Sci. 2018; 9: 7218
    • 24a Yang W, Yang S, Li P, Wang L. Chem. Commun. 2015; 51: 7520
    • 24b Xia D, Miao T, Li P, Wang L. Chem. Asian J. 2015; 10: 1919
  • 25 Yang D, Huang B, Wei W, Li J, Lin G, Liu Y, Ding J, Sun P, Wang H. Green Chem. 2016; 18: 5630
  • 26 Wang H, Lu Q, Chiang CW, Luo Y, Zhou J, Wang G, Lei A. Angew. Chem. Int. Ed. 2017; 56: 595
  • 27 Huang M.-H, Zhu Y.-L, Hao W.-J, Wang A.-F, Wang D.-C, Liu F, Wei P, Tu S.-J, Jiang B. Adv. Synth. Catal. 2017; 359: 2229
  • 28 Mei Y, Zhao L, Liu Q, Ruan S, Wang L, Li P. Green Chem. 2020; 22: 2270
  • 29 Zhang G, Zhang L, Yi H, Luo Y, Qi X, Tung C.-H, Wu L.-Z, Lei A. Chem. Commun. 2016; 52: 10407
  • 30 Chaudhary R, Natarajan P. ChemistrySelect 2017; 2: 6458
    • 31a Bagal DB, Kachkovskyi G, Knorn M, Rawner T, Bhanage BM, Reiser O. Angew. Chem. Int. Ed. 2015; 54: 6999
    • 31b Hossain A, Engl S, Lutsker E, Reiser O. ACS Catal. 2019; 9: 1103
  • 32 Májek M, Neumeier M, Jacobi von Wangelin A. ChemSusChem 2017; 10: 151
  • 33 Rawner T, Knorn M, Lutsker E, Hossain A, Reiser O. J. Org. Chem. 2016; 81: 7139
  • 34 Pagire SK, Paria S, Reiser O. Org. Lett. 2016; 18: 2106
  • 35 Niu T.-f, Cheng J, Zhuo C.-l, Jiang D.-y, Shu X.-g, Ni B.-q. Tetrahedron Lett. 2017; 58: 3667
  • 36 Niu T, Jiang D, Ni B. Tetrahedron Lett. 2017; 58: 4299
  • 37 Mao L.-L, Zheng D.-G, Zhu X.-H, Zhou A.-X, Yang S.-D. Org. Chem. Front. 2018; 5: 232
  • 38 Liu C, Yang YJ, Dong JY, Zhou MD, Li L, Wang H. Org. Chem. Front. 2019; 6: 3944
  • 39 Tang N, Yang S, Wu X, Zhu C. Tetrahedron 2019; 75: 1639
  • 40 Niu T.-f, Lin D, Xue L.-s, Jiang D.-y, Ni B.-q. Synlett 2018; 29: 364
  • 41 Chakrasali P, Kim K, Jung YS, Kim H, Han SB. Org. Lett. 2018; 20: 7509
  • 42 Hou H, Li H, Xu Y, Song C, Wang C, Shi Y, Han Y, Yan C, Zhu S. Adv. Synth. Catal. 2018; 360: 4325
  • 43 Parisotto S, Garreffa G, Canepa C, Diana E, Pellegrino F, Priola E, Prandi C, Maurino V, Deagostino A. ChemPhotoChem 2017; 1: 56
  • 44 Jiang Y.-Q, Li J, Feng Z.-W, Xu G.-Q, Shi X, Ding Q.-J, Li W, Ma C.-H, Yu B. Adv. Synth. Catal. 2020; 362: 2609
    • 45a Zheng D, Wu J. Sulfur Dioxide Surrogates . In Sulfur Dioxide Insertion Reactions for Organic Synthesis . Zheng D, Wu J. Springer Singapore; Singapore: 2017: 7-10
    • 45b Emmett EJ, Willis MC. Asian J. Org. Chem. 2015; 4: 602
    • 46a Santos PS, Mello MT. S. J. Mol. Struct. 1988; 178: 121
    • 46b Ye S, Qiu G, Wu J. Chem. Commun. 2019; 55: 1013
    • 46c Woolven H, González-Rodríguez C, Marco I, Thompson AL, Willis MC. Org. Lett. 2011; 13: 4876
  • 47 Hofman K, Liu N.-W, Manolikakes G. Chem. Eur. J. 2018; 24: 11852
  • 48 Liu T, Ding Y, Fan X, Wu J. Org. Chem. Front. 2018; 5: 3153
  • 49 Ye S, Li X, Xie W, Wu J. Asian J. Org. Chem. 2019; 8: 893
  • 50 Liu T, Li Y, Lai L, Cheng J, Sun J, Wu J. Org. Lett. 2018; 20: 3605
    • 51a Gong X, Yang M, Liu JB, He FS, Wu J. Org. Chem. Front. 2020; 7: 938
    • 51b Gong X, Yang M, Liu JB, He FS, Fan X, Wu J. Green Chem. 2020; 22: 1906
    • 52a Gong X, Ding Y, Fan X, Wu J. Adv. Synth. Catal. 2017; 359: 2999
    • 52b Ye S, Zheng D, Wu J, Qiu G. Chem. Commun. 2019; 55: 2214
  • 53 Wang X, Kuang Y, Ye S, Wu J. Chem. Commun. 2019; 55: 14962
  • 54 Ni B, Zhang B, Han J, Peng B, Shan Y, Niu T. Org. Lett. 2020; 22: 670
    • 55a Masih D, Ma Y, Rohani S. Appl. Catal. B 2017; 206: 556
    • 55b Ong W.-J, Tan L.-L, Ng YH, Yong S.-T, Chai S.-P. Chem. Rev. 2016; 116: 7159
    • 55c Peng L, Zheng R.-r, Feng D.-w, Yu H, Dong X.-t. Arabian J. Chem. 2020; 13: 4275
    • 55d Zhou Z, Zhang Y, Shen Y, Liu S, Zhang Y. Chem. Soc. Rev. 2018; 47: 2298
  • 56 Gong X, Chen J, Lai L, Cheng J, Sun J, Wu J. Chem. Commun. 2018; 54: 11172
  • 57 Ye S, Li Y, Wu J, Li Z. Chem. Commun. 2019; 55: 2489
  • 58 Li Y, Liu JB, He FS, Wu J. Chin. J. Chem. 2020; 38: 361
  • 59 Zhang J, Li X, Xie W, Ye S, Wu J. Org. Lett. 2019; 21: 4950
  • 60 Herrera F, Luna A, Almendros P. Org. Lett. 2020; 22: 9490
  • 61 Cao S, Hong W, Ye Z, Gong L. Nat. Commun. 2021; 12: 2377
  • 62 Liu N.-W, Chen Z, Herbert A, Ren H, Manolikakes G. Eur. J. Org. Chem. 2018; 5725
  • 63 Chen Z, Liu N.-W, Bolte M, Ren H, Manolikakes G. Green Chem. 2018; 20: 3059
  • 64 Sun D, Yin K, Zhang R. Chem. Commun. 2018; 54: 1335
  • 65 Nair AM, Halder I, Khan S, Volla CM. R. Adv. Synth. Catal. 2020; 362: 224
  • 66 Breton-Patient C, Naud-Martin D, Mahuteau-Betzer F, Piguel S. Eur. J. Org. Chem. 2020; 6653
  • 67 Ge Q.-Q, Qian J.-S, Xuan J. J. Org. Chem. 2019; 84: 8691
  • 68 Li X, Wang M, Wang Z, Wang L. Asian J. Org. Chem. 2019; 8: 1426
  • 69 Chawla R, Jaiswal S, Dutta PK, Yadav LD. S. Tetrahedron Lett. 2020; 61: 151898
    • 70a Liu Q, Liu F, Yue H, Zhao X, Li J, Wei W. Adv. Synth. Catal. 2019; 361: 5277
    • 70b Lv Y, Liu Q, Liu F, Yue H, Li JS, Wei W. Tetrahedron Lett. 2020; 61: 151335
  • 71 Chen Y, McNamara N, May O, Pillaiyar T, Blakemore DC, Ley SV. Org. Lett. 2020; 22: 5746
  • 72 Min W, Guo G, Yang C, Huo C. Tetrahedron Lett. 2020; 61: 152029
  • 73 Xie L, Zhen X, Huang S, Su X, Lin M, Li Y. Green Chem. 2017; 19: 3530
  • 74 Huang X, Luo S, Burghaus O, Webster RD, Harms K, Meggers E. Chem. Sci. 2017; 8: 7126
  • 75 Yin G, Zhu M, Fu W. Heterocycl. Commun. 2017; 23: 275
  • 76 Ghiazza C, Khrouz L, Monnereau C, Billard T, Tlili A. Chem. Commun. 2018; 54: 9909
  • 77 Zhang R, Xu P, Wang S.-Y, Ji S.-J. J. Org. Chem. 2019; 84: 12324
  • 78 Li Y, Xie W, Jiang X. Chem. Eur. J. 2015; 21: 16059
  • 79 Li J, Bao W, Zhang Y, Rao Y. Eur. J. Org. Chem. 2019; 7175
  • 80 Kibriya G, Mondal S, Hajra A. Org. Lett. 2018; 20: 7740
  • 81 Wang S, Cheng B.-Y, Sršen M, König B. J. Am. Chem. Soc. 2020; 142: 7524
  • 82 Shieh Y.-C, Du K, Basha RS, Xue Y.-J, Shih B.-H, Li L, Lee C.-F. J. Org. Chem. 2019; 84: 6223
  • 83 Zhao G, Kaur S, Wang T. Org. Lett. 2017; 19: 3291
  • 84 Kaur S, Zhao G, Busch E, Wang T. Org. Biomol. Chem. 2019; 17: 1955
  • 85 Pramanik M, Choudhuri K, Mathuri A, Mal P. Chem. Commun. 2020; 56: 10211
  • 86 Czyz ML, Weragoda GK, Monaghan R, Connell TU, Brzozowski M, Scully AD, Burton J, Lupton DW, Polyzos A. Org. Biomol. Chem. 2018; 16: 1543
  • 87 Blank L, Fagnoni M, Protti S, Rueping M. Synthesis 2019; 51: 1243
  • 88 Meyer AU, Berger AL, König B. Chem. Commun. 2016; 52: 10918
  • 89 Kim T, McCarver SJ, Lee C, MacMillan DW. C. Angew. Chem. Int. Ed. 2018; 57: 3488
  • 90 Koohgard M, Hosseini-Sarvari M. Catal. Sci. Technol. 2020; 10: 6825
  • 91 Luo Q, Mao R, Zhu Y, Wang Y. J. Org. Chem. 2019; 84: 13897
    • 92a The Treatment of Epilepsy, 4th ed. Shorvon S, Perucca E, Engel JJr. Wiley-Blackwell; London: 2016: 680-688
    • 92b Mukarram J, Mohammed S, Yehanathsa MA, Dat-Topant SJ, Mushtaqeali S. WO 2005044808, 2005
  • 93 Chatgilialoglu C, Griller D, Rossini S. J. Org. Chem. 1989; 54: 2734
  • 94 Hell SM, Meyer CF, Laudadio G, Misale A, Willis MC, Noël T, Trabanco AA, Gouverneur V. J. Am. Chem. Soc. 2020; 142: 720
  • 95 Zhang M, Ding X, Lu A, Kang J, Gao Y, Wang Z, Li H, Wang Q. Org. Chem. Front. 2021; 8: 961
  • 96 Li Y, Zheng D, Li Z, Wu J. Org. Chem. Front. 2016; 3: 574
  • 97 Liu N.-W, Liang S, Manolikakes G. Adv. Synth. Catal. 2017; 359: 1308
  • 98 Xiang Y, Li Y, Kuang Y, Wu J. Chem. Eur. J. 2017; 23: 1032