Recent Advances in Electrochemical Oxidative Cross-Coupling for the Construction of C–S Bonds

Chunlan Song; Kun Liu; Xin Dong; Chien-Wei Chiang; Aiwen Lei

doi:10.1055/s-0037-1611753

Synlett, Table of Contents

Synlett 2019; 30(10): 1149-1163
DOI: 10.1055/s-0037-1611753

cluster

Recent Advances in Electrochemical Oxidative Cross-Coupling for the Construction of C–S Bonds

Chunlan Song

^aCollege of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, Hubei, P. R. of China Email: aiwenlei@whu.edu.cn Email: cwchiang@whu.edu.cn

,

Kun Liu

^aCollege of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, Hubei, P. R. of China Email: aiwenlei@whu.edu.cn Email: cwchiang@whu.edu.cn

,

Xin Dong

^aCollege of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, Hubei, P. R. of China Email: aiwenlei@whu.edu.cn Email: cwchiang@whu.edu.cn

,

Chien-Wei Chiang*

^aCollege of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, Hubei, P. R. of China Email: aiwenlei@whu.edu.cn Email: cwchiang@whu.edu.cn

,

Aiwen Lei*

^aCollege of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, Hubei, P. R. of China Email: aiwenlei@whu.edu.cn Email: cwchiang@whu.edu.cn

^bNational Research Center for Carbohydrate Synthesis Jiangxi Normal University, Nanchang 330022, Jiangxi, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Published as part of the Cluster Electrochemical Synthesis and Catalysis

Abstract

With the importance of sulfur-containing organic molecules, developing methodologies toward C–S bond formation is a long-standing goal, and, to date, considerable progress has been made in this area. Recent electrochemical oxidative cross-coupling reactions for C–S bond formation allow the synthesis of sulfur-containing molecules from more effective synthetic routes with high atom economy under mild conditions. In this review, we highlight the vital progress in this novel research arena with an emphasis on the synthetic and mechanistic aspects of the organic electrochemistry reactions.

1 Introduction

2 Electrochemical Oxidative Sulfonylation for the Formation of C–S Bonds

2.1 Applications of Sulfinic Acid Derivatives for the Formation of C–S Bonds

2.2 Applications of Sulfonylhydrazide Derivatives for the Formation of C–S Bonds

3 Electrochemical Oxidative Thiolation for the Formation of C–S Bonds

3.1 Applications of Disulfide Derivatives for the Formation of C–S Bonds

3.2 Applications of Thiophenol Derivatives for the Formation of C–S Bonds

4 Electrochemical Oxidative Thiocyanation for the Formation of C–S Bonds

5 Electrochemical Oxidative Cyclization for the Formation of C–S Bonds

6 Conclusion

Key words

electrochemistry - C–S bond formation - sulfonylation - thiolation - thiocyanation - cyclization

Full Text

References

References

1a Conroy S, Kindon N, Kellam B, Stocks MJ. J. Med. Chem. 2016; 59: 9981
1b Feng M, Tang B, Liang SH, Jiang X. Curr. Top. Med. Chem. 2016; 16: 1200
1c Ilardi EA, Vitaku E, Njardarson JT. J. Med. Chem. 2014; 57: 2832
1d Karabanovich G, Zemanová J, Smutný T, Székely R, Šarkan M, Centárová I, Vocat A, Pávková I, Čonka P, Němeček J, Stolaříková J, Vejsová M, Vávrová K, Klimešová V, Hrabálek A, Pávek P, Cole ST, Mikušová K, Roh J. J. Med. Chem. 2016; 59: 2362
1e Ling C, Fu L, Gao S, Chu W, Wang H, Huang Y, Chen X, Yang Y. J. Med. Chem. 2014; 57: 4772
1f Liu J, Yang J, Yang Q, Wang G, Li Y. Adv. Funct. Mater. 2005; 15: 1297
1g Scott KA, Njardarson JT. Top. Curr. Chem. 2018; 376: 5

2a Hartwig JF. Nature 2008; 455: 314
2b Lu Q, Zhang J, Wei F, Qi Y, Wang H, Liu Z, Lei A. Angew. Chem. Int. Ed. 2013; 52: 7156
2c Lu Q, Zhang J, Zhao G, Qi Y, Wang H, Lei A. J. Am. Chem. Soc. 2013; 135: 11481
2d Shen C, Zhang P, Sun Q, Bai S, Hor TS. A, Liu X. Chem. Soc. Rev. 2015; 44: 291
2e Xi Y, Dong B, McClain EJ, Wang Q, Gregg TL, Akhmedov NG, Petersen JL, Shi X. Angew. Chem. Int. Ed. 2014; 53: 4657

3a Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
3b Eichman CC, Stambuli JP. Molecules 2011; 16: 590
3c Kondo T, Mitsudo T.-a. Chem. Rev. 2000; 100: 3205
3d Lee C.-F, Liu Y.-C, Badsara SS. Chem. Asian J. 2014; 9: 706

4a Itoh T, Mase T. Org. Lett. 2004; 6: 4587
4b Mispelaere-Canivet C, Spindler J.-F, Perrio S, Beslin P. Tetrahedron 2005; 61: 5253

5a Herradura PS, Pendola KA, Guy RK. Org. Lett. 2000; 2: 2019
5b Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400

6a Correa A, Carril M, Bolm C. Angew. Chem. Int. Ed. 2008; 47: 2880
6b Lin Y.-Y, Wang Y.-J, Lin C.-H, Cheng J.-H, Lee C.-F. J. Org. Chem. 2012; 77: 6100
6c Wu W.-Y, Wang J.-C, Tsai F.-Y. Green Chem. 2009; 11: 326

7 Wong Y.-C, Jayanth TT, Cheng C.-H. Org. Lett. 2006; 8: 5613
8 Jammi S, Barua P, Rout L, Saha P, Punniyamurthy T. Tetrahedron Lett. 2008; 49: 1484

9a Zhao Y, Wang H, Hou X, Hu Y, Lei A, Zhang H, Zhu L. J. Am. Chem. Soc. 2006; 128: 15048
9b Li C.-J. Acc. Chem. Res. 2009; 42: 335
9c Chen M, Zheng X, Li W, He J, Lei A. J. Am. Chem. Soc. 2010; 132: 4101
9d Le Bras J, Muzart J. Chem. Rev. 2011; 111: 1170
9e Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
9f Shi W, Liu C, Lei A. Chem. Soc. Rev. 2011; 40: 2761
9g Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
9h He C, Guo S, Ke J, Hao J, Xu H, Chen H, Lei A. J. Am. Chem. Soc. 2012; 134: 5766
9i Zhang G, Liu C, Yi H, Meng Q, Bian C, Chen H, Jian J.-X, Wu L.-Z, Lei A. J. Am. Chem. Soc. 2015; 137: 9273
9j Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
9k Liu C, Liu D, Lei A. Acc. Chem. Res. 2014; 47: 3459
9l Song C, Yi H, Dou B, Li Y, Singh AK, Lei A. Chem. Commun. 2017; 53: 3689
9m Liu C, Yuan J, Gao M, Tang S, Li W, Shi R, Lei A. Chem. Rev. 2015; 115: 12138
9n Song C, Dong X, Yi H, Chiang C.-W, Lei A. ACS Catal. 2018; 8: 2195

10a Sperry JB, Wright DL. Chem. Soc. Rev. 2006; 35: 605
10b Jutand A. Chem. Rev. 2008; 108: 2300
10c Yoshida J.-i, Kataoka K, Horcajada R, Nagaki A. Chem. Rev. 2008; 108: 2265
10d Waldvogel SR, Lips S, Selt M, Riehl B, Kampf CJ. Chem. Rev. 2018; 118: 6706
10e Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
10f Jiang Y, Xu K, Zeng C. Chem. Rev. 2018; 118: 4485
10g Kärkäs MD. Chem. Soc. Rev. 2018; 47: 5786
10h Liang S, Xu K, Zeng C.-C, Tian H.-Y, Sun B.-G. Adv. Synth. Catal. 2018; 360: 4266
10i Liu K, Song C, Lei A. Org. Biomol. Chem. 2018; 16: 2375
10j Moeller KD. Chem. Rev. 2018; 118: 4817
10k Tang S, Liu Y, Lei A. Chem 2018; 4: 27

11a Xu G, Moeller KD. Org. Lett. 2010; 12: 2590
11b Xu H.-C, Moeller KD. J. Am. Chem. Soc. 2010; 132: 2839
11c Ye K.-Y, Pombar G, Fu N, Sauer GS, Keresztes I, Lin S. J. Am. Chem. Soc. 2018; 140: 2438
11d Fu N, Sauer GS, Lin S. J. Am. Chem. Soc. 2017; 139: 15548
11e Fu N, Sauer GS, Saha A, Loo A, Lin S. Science 2017; 357: 575
11f Liu K, Tang S, Huang P, Lei A. Nat. Commun. 2017; 8: 775
11g Sauermann N, Meyer TH, Tian C, Ackermann L. J. Am. Chem. Soc. 2017; 139: 18452
11h Tang S, Wang S, Liu Y, Cong H, Lei A. Angew. Chem. Int. Ed. 2018; 57: 4737
11i Yang Q.-L, Li Y.-Q, Ma C, Fang P, Zhang X.-J, Mei T.-S. J. Am. Chem. Soc. 2017; 139: 3293
11j Zhao H.-B, Hou Z.-W, Liu Z.-J, Zhou Z.-F, Song J, Xu H.-C. Angew. Chem. Int. Ed. 2017; 56: 587
11k Rafiee M, Wang F, Hruszkewycz DP, Stahl SS. J. Am. Chem. Soc. 2018; 140: 22

12a Beaulieu C, Guay D, Wang Z, Evans DA. Tetrahedron Lett. 2004; 45: 3233
12b Meadows DC, Gervay-Hague J. Med. Res. Rev. 2006; 26: 793
12c Yang H, Carter RG, Zakharov LN. J. Am. Chem. Soc. 2008; 130: 9238
12d Alba A.-NR, Companyó X, Rios R. Chem. Soc. Rev. 2010; 39: 2018
12e Nielsen M, Jacobsen CB, Holub N, Paixão MW, Jørgensen KA. Angew. Chem. Int. Ed. 2010; 49: 2668
12f Aziz J, Messaoudi S, Alami M, Hamze A. Org. Biomol. Chem. 2014; 12: 9743
12g Deeming AS, Emmett EJ, Richards-Taylor CS, Willis MC. Synthesis 2014; 46: 2701
12h Gauthier DR, Yoshikawa N. Org. Lett. 2016; 18: 5994
12i Liu N.-W, Liang S, Manolikakes G. Synthesis 2016; 48: 1939

13 Luo Y.-C, Pan X.-J, Yuan G.-Q. Tetrahedron 2015; 71: 2119
14 Qian P, Bi M, Su J, Zha Z, Wang Z. J. Org. Chem. 2016; 81: 4876
15 Chan C.-K, Lo N.-C, Chen P.-Y, Chang M.-Y. Synthesis 2017; 49: 4469
16 Zheng M.-W, Yuan X, Cui Y.-S, Qiu J.-K, Li G, Guo K. Org. Lett. 2018; 20: 7784
17 Gao Y, Mei H, Han J, Pan Y. Chem. Eur. J. 2018; 24: 17205

18a Zeng C.-C, Liu C.-F, Zeng J, Zhong R.-G. J. Electroanal. Chem. 2007; 608: 85
18b Nematollahi D, Varmaghani F. Electrochim. Acta 2008; 53: 3350
18c Nematollahi D, Esmaili R. Tetrahedron Lett. 2010; 51: 4862
18d Nematollahi D, Amani A. J. Electroanal. Chem. 2011; 651: 72
18e Sharafi-Kolkeshvandi M, Nematollahi D, Nikpour F. Synthesis 2017; 49: 1555

19 Nourmohammadi F, Golabi SM, Saadnia A. J. Electroanal. Chem. 2002; 529: 12

20a La Regina G, Coluccia A, Brancale A, Piscitelli F, Gatti V, Maga G, Samuele A, Pannecouque C, Schols D, Balzarini J, Novellino E, Silvestri R. J. Med. Chem. 2011; 54: 1587
20b Ivachtchenko AV, Golovina ES, Kadieva MG, Kysil VM, Mitkin OD, Tkachenko SE, Okun IM. J. Med. Chem. 2011; 54: 8161
20c Liu KG, Robichaud AJ, Bernotas RC, Yan Y, Lo JR, Zhang M.-Y, Hughes ZA, Huselton C, Zhang GM, Zhang JY, Kowal DM, Smith DL, Schechter LE, Comery TA. J. Med. Chem. 2010; 53: 7639
20d Becker DP, Barta TE, Bedell LJ, Boehm TL, Bond BR, Carroll J, Carron CP, DeCrescenzo GA, Easton AM, Freskos JN, Funckes-Shippy CL, Heron M, Hockerman S, Howard CP, Kiefer JR, Li MH, Mathis KJ, McDonald JJ, Mehta PP, Munie GE, Sunyer T, Swearingen CA, Villamil CI, Welsch D, Williams JM, Yu Y, Yao J. J. Med. Chem. 2010; 53: 6653
20e Nuti E, Panelli L, Casalini F, Avramova SI, Orlandini E, Santamaria S, Nencetti S, Tuccinardi T, Martinelli A, Cercignani G, D'Amelio N, Maiocchi A, Uggeri F, Rossello A. J. Med. Chem. 2009; 52: 6347

21 Feng M.-L, Xi L.-Y, Chen S.-Y, Yu X.-Q. Eur. J. Org. Chem. 2017; 2746
22 Pan X.-J, Gao J, Yuan G.-Q. Tetrahedron 2015; 71: 5525

23a Li X, Xu X, Zhou C. Chem. Commun. 2012; 48: 12240
23b Wei W, Liu C, Yang D, Wen J, You J, Suo Y, Wang H. Chem. Commun. 2013; 49: 10239
23c Yang Y, Tang L, Zhang S, Guo X, Zha Z, Wang Z. Green Chem. 2014; 16: 4106
23d Li S, Li X, Yang F, Wu Y. Org. Chem. Front. 2015; 2: 1076
23e Yang Y, Bao Y, Guan Q, Sun Q, Zha Z, Wang Z. Green Chem. 2017; 19: 112

24 Terent’ev AO, Mulina OM, Pirgach DA, Ilovaisky AI, Syroeshkin MA, Kapustina NI, Nikishin GI. Tetrahedron 2017; 73: 6871
25 Zhao Y, Lai Y.-L, Du K.-S, Lin D.-Z, Huang J.-M. J. Org. Chem. 2017; 82: 9655
26 Yuan Y, Cao Y, Lin Y, Li Y, Huang Z, Lei A. ACS Catal. 2018; 8: 10871
27 Yuan Y, Yu Y, Qiao J, Liu P, Yu B, Zhang W, Liu H, He M, Huang Z, Lei A. Chem. Commun. 2018; 54: 11471

28a Do QT, Elothmani D, Guillanton GL. Tetrahedron Lett. 1998; 39: 4657
28b Do QT, Elothmani D, Simonet J, Guillanton GL. Electrochim. Acta 2005; 50: 4792

29 Töteberg-Kaulen S, Steckhan E. Tetrahedron 1988; 44: 4389

30a Matsumoto K, Suga S, Yoshida J.-i. Org. Biomol. Chem. 2011; 9: 2586
30b Yoshida J.-i, Shimizu A, Hayashi R. Chem. Rev. 2018; 118: 4702

31a Shunsuke F, Kouichi M, Seiji S, Jun-ichi Y. Chem. Lett. 2009; 38: 1186
31b Fujie S, Matsumoto K, Suga S, Nokami T, Yoshida J.-i. Tetrahedron 2010; 66: 2823
31c Matsumoto K, Sanada T, Shimazaki H, Shimada K, Hagiwara S, Fujie S, Ashikari Y, Suga S, Kashimura S, Yoshida J.-i. Asian J. Org. Chem. 2013; 2: 325
31d Matsumoto K, Shimazaki H, Sanada T, Shimada K, Hagiwara S, Suga S, Kashimura S, Yoshida J.-i. Chem. Lett. 2013; 42: 843

32 Matsumoto K, Kozuki Y, Ashikari Y, Suga S, Kashimura S, Yoshida J.-i. Tetrahedron Lett. 2012; 53: 1916
33 Suga S, Okajima M, Fujiwara K, Yoshida J.-i. J. Am. Chem. Soc. 2001; 123: 7941
34 Chen C, Niu P, Shen Z, Li M. J. Electrochem. Soc. 2018; 165: G67
35 Hosseinian A, Ahmadi S, Nasab FA. H, Mohammadi R, Vessally E. Top. Curr. Chem. 2018; 376: 39
36 Nematollahi D, Tammari E. J. Org. Chem. 2005; 70: 7769
37 Zeng C.-C, Liu F.-J, Ping D.-W, Hu L.-M, Cai Y.-L, Zhong R.-G. Tetrahedron 2009; 65: 4505
38 Fakhari AR, Hosseiny Davarani SS, Ahmar H, Hasheminasab K, Khavasi HR. J. Heterocycl. Chem. 2009; 46: 443

39a Kashiwagi T, Amemiya F, Fuchigami T, Atobe M. Chem. Commun. 2012; 48: 2806
39b Kashiwagi T, Amemiya F, Fuchigami T, Atobe M. J. Flow Chem. 2012; 3: 17

40 Wang P, Tang S, Huang P, Lei A. Angew. Chem. Int. Ed. 2017; 56: 3009
41 Yuan Y, Cao Y, Qiao J, Lin Y, Jiang X, Weng Y, Tang S, Lei A. Chin. J. Chem. 2019; 37: 49
42 Yuan Y, Chen Y, Tang S, Huang Z, Lei A. Sci. Adv. 2018; 4: eaat5312
43 Wang Y, Deng L, Mei H, Du B, Han J, Pan Y. Green Chem. 2018; 20: 3444
44 Ogawa KA, Boydston AJ. Org. Lett. 2014; 16: 1928

45a Nagamachi T, Fourrey JL, Torrence PF, Waters JA, Witkop B. J. Med. Chem. 1974; 17: 403
45b Yagodinets PI, Skripskaya OV, Prodanchuk NG, Chernyuk IN, Sinchenko VG, Dozirtsiv GM, Pityk MY. Pharm. Chem. J. 1995; 29: 54
45c Elhalem E, Bailey BN, Docampo R, Ujváry I, Szajnman SH, Rodriguez JB. J. Med. Chem. 2002; 45: 3984
45d Kokorekin VA, Terent’ev AO, Ramenskaya GV, Grammatikova NÉ, Rodionova GM, Ilovaiskii AI. Pharm. Chem. J. 2013; 47: 422

46 Kelly TR, Kim MH, Curtis AD. M. J. Org. Chem. 1993; 58: 5855
47 Fritz HP, Ecker P. Chem. Ber. 1981; 114: 3643

48a Krishnan P, Gurjar VG. Synth. Commun. 1992; 22: 2741
48b Krishnan P, Gurjar VG. J. Appl. Electrochem. 1995; 25: 792
48c Gitkis A, Becker JY. Electrochim. Acta 2010; 55: 5854

49 Fotouhi L, Nikoofar K. Tetrahedron Lett. 2013; 54: 2903

50a Kokorekin VA, Sigacheva VL, Petrosyan VA. Tetrahedron Lett. 2014; 55: 4306
50b Zhang X, Wang C, Jiang H, Sun L. RSC Adv. 2018; 8: 22042

51 Liang S, Zeng C.-C, Tian H.-Y, Sun B.-G, Luo X.-G, Ren F.-z. Adv. Synth. Catal. 2018; 360: 1444
52 Kang L.-S, Luo M.-H, Lam CM, Hu L.-M, Little RD, Zeng C.-C. Green Chem. 2016; 18: 3767
53 Sinhmar A, Sharma A, Rajak H, Pathak DP. J. Enzyme Inhib. Med. Chem. 2013; 28: 240

54a Cheng Y, Yang J, Qu Y, Li P. Org. Lett. 2012; 14: 98
54b Wang H, Wang L, Shang J, Li X, Wang H, Gui J, Lei A. Chem. Commun. 2012; 48: 76

55 Tabaković I, Trkovnik M, Batušić M, Tabaković K. Synthesis 1979; 590
56 Qian X.-Y, Li S.-Q, Song J, Xu H.-C. ACS Catal. 2017; 7: 2730
57 Folgueiras-Amador AA, Qian X.-Y, Xu H.-C, Wirth T. Chem. Eur. J. 2018; 24: 487
58 Wang H.-B, Huang J.-M. Adv. Synth. Catal. 2016; 358: 1975
59 Wang P, Tang S, Lei A. Green Chem. 2017; 19: 2092
60 Wang Z.-Q, Meng X.-J, Li Q.-Y, Tang H.-T, Wang H.-S, Pan Y.-M. Adv. Synth. Catal. 2018; 360: 4043
61 Jiang Y.-Y, Liang S, Zeng C.-C, Hu L.-M, Sun B.-G. Green Chem. 2016; 18: 6311
62 Wen J, Shi W, Zhang F, Liu D, Tang S, Wang H, Lin X.-M, Lei A. Org. Lett. 2017; 19: 3131