Progress in S–X Bond Formation by Halogen-Mediated Electrochemical Reactions

Juan Du; Ya-long Du; Qing-wen Gui

doi:10.1055/a-2096-4349

Synthesis, Table of Contents

Synthesis 2023; 55(18): 2799-2816
DOI: 10.1055/a-2096-4349

review

Special Issue Electrochemical Organic Synthesis

Progress in S–X Bond Formation by Halogen-Mediated Electrochemical Reactions

Authors

Juan Du

^aGuangxi Key Laboratory of Natural Polymer Chemistry and Physics, College of Chemistry and Materials, Nanning Normal University, Nanning, Guangxi 530001, P. R. of China
Ya-long Du

^aGuangxi Key Laboratory of Natural Polymer Chemistry and Physics, College of Chemistry and Materials, Nanning Normal University, Nanning, Guangxi 530001, P. R. of China
Qing-wen Gui ∗

^bCollege of Chemistry and Materials Science, Hunan Agricultural University, Changsha, 410128, P. R. of China

Abstract

All articles of this category

Abstract

Sulfur-containing compounds are very common and important heteroatom skeletons and are widely found in natural products, pharmaceuticals and bioactive compounds. Moreover, the development of synthetic routes to organosulfur compounds has attracted considerable attention due to their wide range of applications in organic chemistry, the pharmaceutical industry and in materials science. As one of most powerful, green and eco-friendly research areas, organic electrosynthesis, in contrast to conventional organic synthesis, can avoid the use of harmful stoichiometric external oxidants or reductants. Importantly, halide salts are widely used as supporting electrolytes and redox catalysts in indirect electrosynthesis to avoid the limitations imposed by high overpotentials in direct electrosynthesis. In recent years, significant progress has been made on the halogen-mediated electrosynthesis of organosulfur compounds. In this review, the scope, limitations and mechanisms of halogen-mediated electrochemical transformations of sulfur-containing compounds are presented and discussed.

1 Introduction

2 S–C Bond Formation

2.1 Organic Thiocyanates

2.2 Sulfonyl Compounds

2.3 Other Sulfides

3 Formation of Other S–X (X = N, O, S, P) Bonds

4 Conclusion and Outlook

Key words

organosulfur compounds - electrosynthesis - halogen-mediated - eco-friendly - sulfonyl compounds - organic thiocyanates

Full Text

References

References

1a Moriarty RM, Naithani R, Surve B. Mini-Rev. Med. Chem. 2007; 7: 827
1b Hwang D, Kim M, Park H, Jeong MI, Jung W, Kim B. Nutrients 2019; 11: 1010
1c Awakawa T, Barra L, Abe I. J. Ind. Microbiol. Biotechnol. 2021; 48: kuab001
1d Zhu HZ, Dronamraju V, Xie W, More SS. Med. Chem. Res. 2021; 30: 305
1e Mustafa M, Winum JY. Expert Opin. Drug Discovery 2022; 17: 501
1f Smith JM, Dixon JA, deGruyter JN, Baran PS. J. Med. Chem. 2019; 62: 2256

2a Supuran CT. Molecules 2017; 22: 1642
2b Hoegberg T, Bengtsson S, De Paulis T, Johansson L, Stroem P, Hall H, Oegren SO. J. Med. Chem. 1990; 33: 1155
2c Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, Anderson GD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC. J. Med. Chem. 1997; 40: 1347
2d Feng M, Tang B, Liang S, Jiang X. Curr. Top. Med. Chem. 2015; 16: 1200
2e Scott KA, Njardarson JT. Analysis of US FDA-Approved Drugs Containing Sulfur Atoms . In Sulfur Chemistry . Jiang X. Springer International Publishing; Cham: 2019: 1-34

3a Wang L, He W, Yu Z. Chem. Soc. Rev. 2013; 42: 599
3b Thanh Binh N. Adv. Synth. Catal. 2017; 359: 1066
3c Zhang X, Chen K, Sun Z, Hu G, Xiao R, Cheng H.-M, Li F. Energy Environ. Sci. 2020; 13: 1076
3d Reddy RJ, Kumari AH. RSC Adv. 2021; 11: 9130
3e Lv Y, Cui H, Meng N, Yue H, Wei W. Chin. Chem. Lett. 2022; 33: 97

4 Kolbe H. J. Prakt. Chem. 1847; 41: 137
5 Baizer MM. J. Electrochem. Soc. 1964; 111: 215

6a Yan H, Hou ZW, Xu HC. Angew. Chem. Int. Ed. 2019; 58: 4592
6b Erchinger JE, Gemmeren M. Asian J. Org. Chem. 2020; 10: 50
6c Li M, Hong J, Xiao W, Yang Y, Qiu D, Mo F. ChemSusChem 2020; 13: 1661
6d Wang X, Xu X, Wang Z, Fang P, Mei T. Chin. J. Org. Chem. 2020; 40: 3738

7a Martins GM, Meirinho AG, Ahmed N, Braga AL, Mendes SR. ChemElectroChem 2019; 6: 5928
7b Liu W, Hao L, Zhang J, Zhu T. ChemSusChem 2022; 15: e202102557
7c Qian BC, Zhu CZ, Shen GB. ACS Omega 2022; 7: 39531
7d Ma X, Huang G, Gao L, Zhan L, Wei W. Chin. J. Org. Chem. 2023; 43: 17
7e Jamshidi M, Amani A, Khazalpour S, Torabi S, Nematollahi D. New J. Chem. 2021; 45: 18246
7f Liang S, Hofman K, Friedrich M, Keller J, Manolikakes G. ChemSusChem 2021; 14: 4878
7g Amri N, Wirth T. Chem. Rec. 2021; 21: 2526
7h Ye Z, Zhang X, Ma W, Zhang F. Green Chem. 2023; 25: 2524
7i Blum SP, Hofman K, Manolikakes G, Waldvogel SR. Chem. Commun. 2021; 57: 8236

8a Liu K, Song C, Lei A. Org. Biomol. Chem. 2018; 16: 2375
8b Lian F, Xu K, Zeng C. Chem. Rec. 2021; 21: 2290

9a Yan YZ, Cui C, Li Z. Chin. J. Org. Chem. 2018; 38: 2501
9b Guo W, Tao KL, Tan W, Zhao MM, Zheng LY, Fan XL. Org. Chem. Front. 2019; 6: 2048
9c Hu B.-L, Song Y.-K, Zhang G, Yao Z, Zhang X.-G. J. Fluorine Chem. 2020; 239: 109640
9d Peng K, Dong ZB. Adv. Synth. Catal. 2021; 363: 1185

10 Castanheiro T, Suffert J, Donnard M, Gulea M. Chem. Soc. Rev. 2016; 45: 494
11 Kang L.-S, Luo M.-H, Lam CM, Hu L.-M, Little RD, Zeng C.-C. Green Chem. 2016; 18: 3767
12 Liang S, Zeng C.-C, Tian H.-Y, Sun B.-G, Luo X.-G, Ren F.-z. Adv. Synth. Catal. 2018; 360: 1444
13 Takenaka T, Honda K, Fujikura T, Niigata K, Tachikawa S, Inukai N. J. Pharm. Pharmacol. 1984; 36: 539
14 Cross PE, Arrowsmith JE, Thomas GN, Gwilt M, Burges RA, Higgins AJ. J. Med. Chem. 1990; 33: 1151
15 Quesnel LB, Al-Najjar AR, Buddhavudhikrai P. J. Appl. Bacteriol. 1978; 45: 397
16 Uchida T, Hayashi K, Kido H, Watanabe M. J. Pharm. Pharmacol. 1992; 44: 39
17 Grell W, Hurnaus R, Griss G, Sauter R, Rupprecht E, Mark M, Luger P, Nar H, Wittneben H, Müller P. J. Med. Chem. 1998; 41: 5219
18 Trost BM, Kalnmals CA. Chemistry 2019; 25: 11193
19 Liu NW, Liang S, Manolikakes G. Synthesis 2016; 48: 1939
20 Luo Y.-C, Pan X.-J, Yuan G.-Q. Tetrahedron 2015; 71: 2119
21 Terent’ev AO, Mulina OM, Pirgach DA, Ilovaisky AI, Syroeshkin MA, Kapustina NI, Nikishin GI. Tetrahedron 2017; 73: 6871
22 Lai YL, Mo Y, Yan S, Zhang S, Zhu L, Luo J, Guo H, Cai J, Liao J. RSC Adv. 2020; 10: 33155
23 Chang M.-Y, Chen P.-Y, Chan C.-K, Lo N.-C. Synthesis 2017; 28: 4469
24 Feng M.-L, Xi L.-Y, Chen S.-Y, Yu X.-Q. Eur. J. Org. Chem. 2017; 2746
25 Zhang Y.-Z, Mo Z.-Y, Wang H.-S, Wen X.-A, Tang H.-T, Pan Y.-M. Green Chem. 2019; 21: 3807
26 Mulina OM, Zhironkina NV, Paveliev SA, Demchuk DV, Terent’ev AO. Org. Lett. 2020; 22: 1818
27 Ye ZP, Gao J, Duan XY, Guan JP, Liu F, Chen K, Xiao JA, Xiang HY, Yang H. Chem. Commun. 2021; 57: 8969

28a Mai WP, Wang JT, Yang LR, Yan JW, Mao P, Xiao YM, Qu LB. Chin. J. Org. Chem. 2014; 34: 1958
28b Heng R, Zard SZ. Tetrahedron Lett. 2015; 56: 3679
28c Chen Z, Zhou Q, Chen QN, Chen P, Xiong BQ, Liang Y, Tang KW, Xie J, Liu Y. Org. Biomol. Chem. 2020; 18: 8677
28d Xiong T, Zhang Q. Chem. Soc. Rev. 2021; 50: 8857

29 Jiang Y.-Y, Liang S, Zeng C.-C, Hu L.-M, Sun B.-G. Green Chem. 2016; 18: 6311
30 Shen ZJ, Huang B, Ma N, Yao L, Yang C, Guo L, Xia W. Adv. Synth. Catal. 2021; 363: 1944
31 Yin Z, Yu Y, Mei H, Han J. Green Chem. 2021; 23: 3256
32 Kim YJ, Kim DY. Tetrahedron Lett. 2019; 60: 1287
33 Zhang TS, Hao WJ, Wang R, Wang SC, Tu SJ, Jiang B. Green Chem. 2020; 22: 4259
34 Zuo HD, Hao WJ, Zhu CF, Guo C, Tu SJ, Jiang B. Org. Lett. 2020; 22: 4471
35 Wen J, Shi W, Zhang F, Liu D, Tang S, Wang H, Lin XM, Lei A. Org. Lett. 2017; 19: 3131
36 Mo ZY, Zhang YZ, Huang GB, Wang XY, Pan YM, Tang HT. Adv. Synth. Catal. 2020; 362: 2160
37 Zhang X, Lu D, Wang Z. Eur. J. Org. Chem. 2021; 4284
38 Aleti RR, Festa AA, Storozhenko OA, Bondarev VL, Segida OO, Paveliev SA, Rybakov VB, Varlamov AV, Voskressensky LG. Org. Lett. 2022; 24: 9337
39 Dong X, Klein M, Waldvogel SR, Morandi B. Angew. Chem. Int. Ed. 2023; 62: e202213630

40a Peng H, Cheng Y, Ni N, Li M, Choudhary G, Chou HT, Lu C.-D, Tai PC, Wang B. ChemMedChem 2009; 4: 1457
40b Mandai T, Yanagi T, Araki K, Morisaki Y, Kawada M, Otera J. J. Am. Chem. Soc. 1984; 106: 3670
40c Kiren S, Padwa A. J. Org. Chem. 2009; 74: 7781
40d Jannapu Reddy R, Haritha Kumari A, Kumar JJ. Org. Biomol. Chem. 2021; 19: 3087

41 Pan X.-J, Gao J, Yuan G.-Q. Tetrahedron 2015; 71: 5525
42 Yavari I, Shaabanzadeh S. Org. Lett. 2020; 22: 464
43 Wei WJ, Zhong YJ, Feng YF, Gao L, Tang HT, Pan YM, Ma XL, Mo ZY. Adv. Synth. Catal. 2022; 364: 726
44 Chen C, Niu P, Shen Z, Li M. J. Electrochem. Soc. 2018; 165: G67
45 Liu X, Cai TC, Guo D, Nong Z, Yang Y, Li Q, Jiang H, Liu X, Gui QW. Chem. Commun. 2022; 58: 657
46 He TJ, Ye Z, Ke Z, Huang JM. Nat. Commun. 2019; 10: 833
47 Lu F, Yang Z, Wang T, Wang T, Zhang Y, Yuan Y, Lei A. Chin. J. Chem. 2019; 37: 547
48 Wan JL, Huang JM. Adv. Synth. Catal. 2022; 364: 2648
49 Li G, Yu K, Yang J, Xu B, Chen Q. J. Org. Chem. 2021; 86: 15946

50a Shibahara F, Murai T. J. Synth. Org. Chem. Jpn. 2011; 69: 28
50b Tavares L, Santos L, Norena CP. Z. Trends Food Sci. Tech. 2021; 114: 232
50c Pan ZY, Brett DJ. L, He GJ, Parkin IP. Adv. Energy Mater. 2022; 12: 2103483

51a Hiroi K. Yakugaku Zasshi 2000; 120: 733
51b Arisawa M, Yamaguchi M. Pure Appl. Chem. 2008; 80: 993
51c Tamai T, Fujiwara K, Higashimae S, Nomoto A, Ogawa A. Org. Lett. 2016; 18: 2114
51d Arisawa M, Yamaguchi M. Synlett 2019; 30: 1621
51e Jang HY. Org. Biomol. Chem. 2021; 19: 8656

52a Ghorab MM, Alsaid MS, Nissan YM. Acta Pol. Pharm. 2014; 71: 603
52b Al-Dosari MS, Ghorab MM, Al-Said MS, Nissan YM. Chem. Pharm. Bull. 2013; 61: 50
52c Ghorab MM, Alsaid MS, Nissan YM, Ashour AE, Al-Mishari AA, Kumar A, Ahmed SF. Chem. Pharm. Bull. 2016; 64: 1747
52d Al-Dosari MS, Ghorab MM, AlSaid MS, Nissan YM, Ahmed AB. Eur. J. Med. Chem. 2013; 69: 373
52e Ghorab MM, Alsaid MS, Al-Dosari MS. Lat. Am. J. Pharm. 2016; 35: 1587

53a Ban S, Xie H, Li Q, Zheng F. Chin. J. Org. Chem. 2011; 31: 1350
53b Ashfaq M, Shah SS. A, Najjam T, Shaheen S, Rivera G. Mini-Rev. Org. Chem. 2013; 10: 160
53c Mondal S. Synth. Commun. 2021; 51: 1023
53d Wu H, Chen X, Sun N, Sanchez-Mendoza A. Synth. Commun. 2021; 51: 2287

54a Wei W, Liu C, Yang D, Wen J, You J, Wang H. Adv. Synth. Catal. 2015; 357: 987
54b Yang K, Ke M, Lin Y, Song Q. Green Chem. 2015; 17: 1395

55 Jiang YY, Wang QQ, Liang S, Hu LM, Little RD, Zeng CC. J. Org. Chem. 2016; 81: 4713
56 Zhang C, Chen Y, Yuan G. Chin. J. Chem. 2016; 34: 1277
57 Terent’ev AO, Mulina OM, Pirgach DA, Syroeshkin MA, Glinushkin AP, Nikishin GI. Mendeleev Commun. 2016; 26: 538
58 Huang H, Yuan G, Li X, Jiang H. Tetrahedron Lett. 2013; 54: 7156
59 Mo Z.-Y, Swaroop TR, Tong W, Zhang Y.-Z, Tang H.-T, Pan Y.-M, Sun H.-B, Chen Z.-F. Green Chem. 2018; 20: 4428
60 Terent’ev AO, Mulina OM, Ilovaisky AI, Kokorekin VA, Nikishin GI. Mendeleev Commun. 2019; 29: 80

61a Zhang X, Cui T, Zhang Y, Gu W, Liu P, Sun P. Adv. Synth. Catal. 2019; 361: 2014
61b Huang P, Wang P, Tang S, Fu Z, Lei A. Angew. Chem. Int. Ed. 2018; 57: 8115

62 Terent’ev AO, Mulina OM, Parshin VD, Kokorekin VA, Nikishin GI. Org. Biomol. Chem. 2019; 17: 3482
63 Zhong Z, Xu P, Ma J, Zhou A. Tetrahedron 2021; 99: 132444

64a Kumar TS, Yang T, Mishra S, Cronin C, Chakraborty S, Shen J.-B, Liang BT, Jacobson KA. J. Med. Chem. 2013; 56: 902
64b McReynolds MD, Dougherty JM, Hanson PR. Chem. Rev. 2004; 104: 2239
64c Lauer AM, Mahmud F, Wu J. J. Am. Chem. Soc. 2011; 133: 9119
64d Liu Y.-C, Lee C.-F. Green Chem. 2014; 16: 357
64e Morrison DC. J. Am. Chem. Soc. 1955; 77: 181

65 Li CY, Liu YC, Li YX, Reddy DM, Lee CF. Org. Lett. 2019; 21: 7833
66 Chen Y, Li M, Gong Z, Shen Z. Phosphorus, Sulfur Silicon Relat. Elem. 2020; 196: 19
67 Zhao L, Liu X, Shi S, Wu Z, Guo X, Shen Z, Li M. Electrochim. Acta 2021; 389: 138748
68 Klein M, Troglauer DL, Waldvogel SR. JACS Au 2023; 3: 575