Synlett 2021; 32(02): 142-158
DOI: 10.1055/s-0040-1707217
cluster
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Sulfur-Containing Heterocycle Formation via Direct C–H Sulfuration with Elemental Sulfur

Saiwen Liu
a   College of Materials and Chemical Engineering, Hunan City University, Yiyang 413000, P. R. of China
b   Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. of China   Email: gjdeng@xtu.edu.cn   Email: hwhuang@xtu.edu.cn
,
Guo-Jun Deng∗
b   Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. of China   Email: gjdeng@xtu.edu.cn   Email: hwhuang@xtu.edu.cn
,
Huawen Huang∗
b   Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. of China   Email: gjdeng@xtu.edu.cn   Email: hwhuang@xtu.edu.cn
› Author AffiliationsWe thank the Normal Project Foundation of Hunan Provincial Education Department (18C0845), the National Natural Science Foundation of China (21871226), and the Science and Technology Planning Project of Hunan Province (2019RS2039) for financial support.
Further Information

Publication History

Received: 29 May 2020

Accepted after revision: 30 June 2020

Publication Date:
07 August 2020 (online)

    Permissions and Reprints All articles of this category


Published as part of the Cluster Modern Heterocycle Synthesis and Functionalization

Abstract

The synthesis of sulfur heterocycles via the construction of C–S bonds has received considerable attention due to their biological value and extensive pharmaceutical application. While diverse sulfurating agents have been developed over the past few decades, in this regard, elemental sulfur, with advantages of low toxicity, odorless nature and chemical stability, has great potential for the construction of diverse sulfur heterocycles through its direct incorporation into the target molecules in a concise way. Direct functionalization of inert C–H bonds can shorten the number of reaction steps and minimize the amount of waste formed. Hence, heteroannulations via direct C–H sulfuration is considered to be an attractive strategy for the synthesis of sulfur heterocycles. In the last few years, a vast array of concise systems have been reported for the synthesis of some valuable sulfur heterocycles such as thiophenes, thienoindoles, thienothiazoles, thiazoles, benzothiazoles, and thiadiazoles through direct C–H sulfuration/annulations with elemental sulfur. These are discussed in detail in this review.

1 Introduction

2 Thiophenes

3 Thienoindoles

4 Thienothiazoles

5 Other Fused Thiophenes

6 Thiazoles

7 Benzothiazoles

8 Thiadiazoles

9 Others

10 Summary and Outlook

Key words

sulfur heterocycles - C–H sulfuration - elemental sulfur - concise synthesis - multicomponent reactions
 

  • References and Notes

    • 1a Domling A, Beck B, Eichelberger U, Sakamuri S, Menon S, Chen QZ, Lu Y, Wessjohann LA. Angew. Chem. Int. Ed. 2006; 45: 7235
      CrossrefPubMed
    • 1b Tomasic T, Katsamakas S, Hodnik Z, Ilas J, Brvar M, Solmajer T, Montalvao S, Tammela P, Banjanac M, Ergovic G, Anderluh M, Peterlin Masic L, Kikelj D. J. Med. Chem. 2015; 58: 5501
      CrossrefPubMed
    • 1c Wojtas KP, Riedrich M, Lu JY, Winter P, Winkler T, Walter S, Arndt HD. Angew. Chem. Int. Ed. 2016; 55: 9772
      CrossrefPubMed
    • 1d Zhao J, Jiang X. Chin. Chem. Lett. 2018; 29: 1079
      CrossrefPubMed
    • 1e Feng MH, Tang BQ, Liang SH, Jiang XF. Curr. Top. Med. Chem. 2016; 16: 1200
      CrossrefPubMed
    • 1f Wang NZ, Saidhareddy P, Jiang XF. Nat. Prod. Rep. 2020; 37: 246
      CrossrefPubMed
  • 2 Kanbe K, Naganawa H, Nakamura KT, Okami Y, Takeuchi T. Biosci., Biotechnol., Biochem. 1993; 57: 632
    CrossrefPubMed
  • 3 Schentag J.-J, Smith LL, Swanson DJ, DeAngelis C, Fracasso JE, Vari A, Vance JW. Am. J. Med. 1984; 77: 43
    CrossrefPubMed
  • 4 Tishler RB, Lamppu DM, Park S, Brendan DP. Cancer Res. 1995; 55: 6021
    CrossrefPubMed
    • 5a Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
      CrossrefPubMed
    • 5b Lee CF, Liu YC, Badsara SS. Chem. Asian J. 2014; 9: 706
      CrossrefPubMed
    • 5c Liu H, Jiang X. Chem. Asian J. 2013; 8: 2546
      CrossrefPubMed
    • 5d Shen C, Zhang P, Sun Q, Bai S, Hor TS, Liu X. Chem. Soc. Rev. 2015; 44: 291
      CrossrefPubMed
    • 5e Qiao Z, Jiang X. Org. Biomol. Chem. 2017; 15: 1942
      CrossrefPubMed
    • 5f Liu J, Zheng L. Adv. Synth. Catal. 2019; 361: 1710
      Crossref
    • 5g Wang M, Li YP, Jiang XF. Aldrichimica Acta 2020; 53: 19
      CrossrefPubMed
    • 6a Nguyen TB. Adv. Synth. Catal. 2017; 359: 1066
      Crossref
    • 6b Nguyen TB. Adv. Synth. Catal. 2020; DOI: 10.1002/adsc.202000535.
      CrossrefPubMed
    • 6c Fedenok LG, Fedotov KY, Pritchina EA, Polyakov NE. Tetrahedron Lett. 2016; 57: 1273
      CrossrefPubMed
    • 6d Huang MQ, Li TJ, Liu JQ, Shatskiy A, Kärkäs MD, Wang XS. Org. Lett. 2020; 22: 3454
      CrossrefPubMed
    • 6e Petrov V, Dooley RJ, Marchione AA, Diaz EL, Clem BS. J. Fluorine Chem. 2019; 225: 1
      CrossrefPubMed
    • 6f Ying J, Wang H, Qi XX, Peng JB, Wu XF. Eur. J. Org. Chem. 2018; 688
      CrossrefPubMed
    • 6g Sakai N, Horikawa S, Ogiwara Y. Synthesis 2018; 50: 565
      CrossrefPubMed
    • 6h Petrov V, Marchione AA, Dooley R. Chem. Commun. 2018; 54: 9298
      CrossrefPubMed
    • 6i Ibragimov AG, Makhmudiyarov GA, Shaibakova MG, Khalilov LM, Dzhemilev UM. Russ. J. Org. Chem. 2019; 55: 1890
      Crossref
    • 7a Liu W, Chen C, Liu H. Adv. Synth. Catal. 2015; 357: 4050
      CrossrefPubMed
    • 7b Zhang G, Yi H, Chen H, Bian C, Liu C, Lei A. Org. Lett. 2014; 16: 6156
      CrossrefPubMed
    • 8a Jiang P, Che X, Liao Y, Huang H, Deng G.-J. RSC Adv. 2016; 6: 41751
      Crossref
    • 8b Nguyen LA, Ngo QA, Retailleau P, Nguyen TB. Green Chem. 2017; 19: 4289
      Crossref
    • 8c Nguyen TB, Ermolenko L, Retailleau P, Al-Mourabit A. Angew. Chem. Int. Ed. 2014; 53: 13808
      CrossrefPubMed
    • 8d Siva ReddyA, Kumara SwamyK. C. Org. Lett. 2015; 17: 2996
      CrossrefPubMed
    • 8e Xie H, Li G, Zhang F, Xiao F, Deng G.-J. Green Chem. 2018; 20: 827
      Crossref
    • 8f Yang Z, Hu R, Li X, Wang X, Gu R, Han S. Tetrahedron Lett. 2017; 58: 2366
      Crossref
    • 8g Wang M, Fan QL, Jiang XF. Org. Lett. 2016; 18: 5756
      CrossrefPubMed
    • 9a Chen FJ, Liao G, Li X, Wu J, Shi BF. Org. Lett. 2014; 16: 5644
      CrossrefPubMed
    • 9b Chen J, Li G, Xie Y, Liao Y, Xiao F, Deng GJ. Org. Lett. 2015; 17: 5870
      CrossrefPubMed
    • 9c Xie H, Cai J, Wang Z, Huang H, Deng GJ. Org. Lett. 2016; 18: 2196
      CrossrefPubMed
    • 9d Chen S, Wang M, Jiang X. Acta Phys.-Chim. Sin. 2019; 35: 954
      CrossrefPubMed
    • 10a Colletto C, Islam S, Julia-Hernandez F, Larrosa I. J. Am. Chem. Soc. 2016; 138: 1677
      CrossrefPubMed
    • 10b Sudo Y, Yamaguchi E, Itoh A. Org. Lett. 2017; 19: 1610
      CrossrefPubMed
    • 10c Tang DT, Collins KD, Glorius F. J. Am. Chem. Soc. 2013; 135: 7450
      CrossrefPubMed
    • 10d Zhang Y, Zhao H, Zhang M, Su W. Angew. Chem. Int. Ed. 2015; 54: 3817
      CrossrefPubMed
    • 11a Bharathiraja G, Sathishkannan G, Punniyamurthy T. J. Org. Chem. 2016; 81: 2670
      CrossrefPubMed
    • 11b Jullien H, Quiclet-Sire B, Tetart T, Zard SZ. Org. Lett. 2014; 16: 302
      CrossrefPubMed
    • 11c Pigulski B, Mecik P, Cichos J, Szafert S. J. Org. Chem. 2017; 82: 1487
      CrossrefPubMed
    • 11d Talbi I, Alayrac C, Lohier JF, Touil S, Witulski B. Org. Lett. 2016; 18: 2656
      CrossrefPubMed
  • 13 Shao W, Kaldas SJ, Yudin AK. Chem. Sci. 2017; 8: 4431
    CrossrefPubMed
  • 14 Thomas J, Jana S, Sonawane M, Fiey B, Balzarini J, Liekens S, Dehaen W. Org. Biomol. Chem. 2017; 15: 3892
    CrossrefPubMed
  • 15 Kavitha K, Srikrishna D, Dubey PK, Aparna P. J. Sulfur Chem. 2019; 40: 195
    Crossref
  • 16 Nguyen TT. T, Le VA, Retailleau P, Nguyen TB. Adv. Synth. Catal. 2019; 362: 160
    CrossrefPubMed
  • 17 Nguyen TB, Pasturaud K, Ermolenko L, Al-Mourabit A. Org. Lett. 2015; 17: 2562
    CrossrefPubMed
  • 18 Nguyen TB, Retailleau P. Green Chem. 2018; 20: 387
    CrossrefPubMed
  • 19 Nguyen TB, Retailleau P. Org. Lett. 2017; 19: 4858
    CrossrefPubMed
  • 20 Nguyen TB, Retailleau P. Org. Lett. 2018; 20: 186
    CrossrefPubMed
  • 21 Wang Z, Qu Z, Xiao F, Huang H, Deng G.-J. Adv. Synth. Catal. 2018; 360: 796
    CrossrefPubMed
    • 22a Adib M, Rajai-Daryasarei S, Pashazadeh R, Jahani M, Amanlou M. Synlett 2018; 29: 1583
      CrossrefPubMed
    • 22b Adib M, Rajai-Daryasarei S, Pashazadeh R, Jahani M, Yazzaf R, Amanlou M. Eur. J. Org. Chem. 2018; 3001
      CrossrefPubMed
  • 23 Sakai S, Sato K, Yoshida K. Tetrahedron Lett. 2020; 61: 151476
    CrossrefPubMed
  • 24 Fukutani T, Hirano K, Satoh T, Miura M. J. Org. Chem. 2011; 76: 2867
    CrossrefPubMed
  • 25 Moon S, Kato M, Nishii Y, Miura M. Adv. Synth. Catal. 2020; 362: 1669
    Crossref
  • 26 Meng L, Fujikawa T, Kuwayama M, Segawa Y, Itami K. J. Am. Chem. Soc. 2016; 138: 10351
    CrossrefPubMed
  • 27 Shoji T, Miura K, Ohta A, Sekiguchi R, Ito S, Endo Y, Nagahata T, Mori S, Okujima T. Org. Chem. Front. 2019; 6: 2801
    Crossref
  • 28 Wu J, He D, Wang Y, Su F, Guo Z, Lin J, Zhang HJ. Org. Lett. 2018; 20: 6117
    CrossrefPubMed
  • 29 Su F, Chen S, Mo X, Wu K, Wu J, Lin W, Lin Z, Lin J, Zhang H.-J, Wen T.-B. Chem. Sci. 2020; 11: 1503
    CrossrefPubMed
  • 30 Chen L, Xia P, Du T, Deng Y, Xiao Y. Org. Lett. 2019; 21: 5529
    CrossrefPubMed
  • 31 Pedras MS, Suchy M. Bioorg. Med. Chem. 2006; 14: 714
    CrossrefPubMed
  • 32 Baert F, Cabanetos C, Allain M, Silvestre V, Leriche P, Blanchard P. Org. Lett. 2016; 18: 1582
    CrossrefPubMed
  • 33 Liao Y, Peng Y, Qi H, Deng GJ, Gong H, Li CJ. Chem. Commun. 2015; 51: 1031
    CrossrefPubMed
  • 34 Li B, Ni P, Huang H, Xiao F, Deng G.-J. Adv. Synth. Catal. 2017; 359: 4300
    CrossrefPubMed
    • 35a Chen S, Li Y, Ni P, Huang H, Deng GJ. Org. Lett. 2016; 18: 5384
      CrossrefPubMed
    • 35b Chen S, Li Y, Ni P, Yang B, Huang H, Deng GJ. J. Org. Chem. 2017; 82: 2935
      CrossrefPubMed
    • 35c Chen S, Wang L, Zhang J, Hao Z, Huang H, Deng GJ. J. Org. Chem. 2017; 82: 11182
      CrossrefPubMed
  • 36 Ni P, Li B, Huang H, Xiao F, Deng G.-J. Green Chem. 2017; 19: 5553
    CrossrefPubMed
  • 37 Nguyen TT, Tran PH. RSC Adv. 2020; 10: 9663
    CrossrefPubMed
  • 38 Zhang H.-L, Wen F, Sheng W.-B, Yin P, Zhang C.-T, Peng C.-Y, Peng D.-M, Liao D.-F, Fu R.-G. Tetrahedron Lett. 2019; 60: 80
    CrossrefPubMed
  • 39 Lu C, Huang H, Tuo X, Jiang P, Zhang F, Deng G.-J. Org. Chem. Front. 2019; 6: 2738
    Crossref
  • 40 Liu Z, Gao R, Lou J, He Y, Yu Z. Adv. Synth. Catal. 2018; 360: 3097
    CrossrefPubMed
  • 41 Liu J, Zhang Y, Yue Y, Wang Z, Shao H, Zhuo K, Lv Q, Zhang Z. J. Org. Chem. 2019; 84: 12946
    CrossrefPubMed
  • 42 Huang H, Xu Z, Ji X, Li B, Deng GJ. Org. Lett. 2018; 20: 4917
    CrossrefPubMed
  • 43 Huang H, Wang Q, Xu Z, Deng GJ. Adv. Synth. Catal. 2018; 361: 591
    CrossrefPubMed
  • 44 Huang H, Qu Z, Ji X, Deng G.-J. Org. Chem. Front. 2019; 6: 1146
    CrossrefPubMed
    • 45a Tang X, Yang J, Zhu Z, Zheng M, Wu W, Jiang H. J. Org. Chem. 2016; 81: 11461
      CrossrefPubMed
    • 45b Zhu Z, Tang X, Cen J, Li J, Wu W, Jiang H. Chem. Commun. 2018; 54: 3767
      CrossrefPubMed
  • 46 Zhou P, Huang Y, Wu W, Yu W, Li J, Zhu Z, Jiang H. Org. Biomol. Chem. 2019; 17: 3424
    CrossrefPubMed
  • 47 Pham PH, Nguyen KX, Pham HT. B, Tran TT, Nguyen TT, Phan NT. S. RSC Adv. 2020; 10: 11024
    CrossrefPubMed
  • 48 Zhang W, Tao SQ, Ge HB, Li Q, Ai ZK, Li XX, Zhang BB, Sun FX, Xu XQ, Du YF. Org. Lett. 2020; 22: 448
    CrossrefPubMed
  • 49 Pham PH, Nguyen KX, Pham HT. B, Nguyen TT, Phan NT. S. Org. Lett. 2019; 21: 8795
    CrossrefPubMed
  • 50 Zhou P, Huang Y, Wu W, Zhou J, Yu W, Jiang H. Org. Lett. 2019; 21: 9976
    CrossrefPubMed
  • 51 Pham PH, Nguyen KX, Nguyen NP, Pham HT. B, Nguyen TT, Phan NT. S. Asian J. Org. Chem. 2020; 9: 622
    CrossrefPubMed
  • 52 Shi T, Zerio CJ, Sivinski J, Ambrose AJ, Moore KT, Buckley T, Kaneko L, Zhang M, Zhang DD, Chapman E. Eur. J. Org. Chem. 2019; 3269
    Crossref
    • 53a Ravi C, Adimurthy S. Chem. Rec. 2017; 17: 1019
      CrossrefPubMed
    • 53b Ravi C, Joshi A, Adimurthy S. Eur. J. Org. Chem. 2017; 3646
  • 54 Semwal R, Ravi C, Saxena S, Adimurthy S. J. Org. Chem. 2019; 84: 14151
    CrossrefPubMed
  • 55 Xu Z, Deng GJ, Zhang F, Chen H, Huang H. Org. Lett. 2019; 21: 8630
    CrossrefPubMed
  • 56 Teja C, Nawaz Khan FR. Org. Lett. 2020; 22: 1726
    CrossrefPubMed
  • 57 Zhang P, Chen W, Liu M, Wu H. Org. Lett. 2019; 21: 9326
    CrossrefPubMed
  • 58 Wilson ZE, Fenner S, Ley SV. Angew. Chem. Int. Ed. 2015; 54: 1284
    CrossrefPubMed
    • 59a Hantzsch A. Ber. Dtsch. Chem. Ges. 1888; 21: 942
      Crossref
    • 59b Kumar SV, Parameshwarappa G, Ila H. J. Org. Chem. 2013; 78: 7362
      CrossrefPubMed
  • 60 Wu M, Jiang Y, An Z, Qi Z, Yan R. Adv. Synth. Catal. 2018; 360: 4236
    CrossrefPubMed
  • 61 Wang X, Qiu X, Wei J, Liu J, Song S, Wang W, Jiao N. Org. Lett. 2018; 20: 2632
    CrossrefPubMed
  • 62 Okesola BO, Mata A. Chem. Soc. Rev. 2018; 47: 3721
    CrossrefPubMed
  • 63 Jiang J, Huang H, Deng G.-J. Green Chem. 2019; 21: 986
    Crossref
  • 64 Fu RG, Wang Y, Xia F, Zhang HL, Sun Y, Yang DW, Wang YW, Yin P. J. Org. Chem. 2019; 84: 12237
    Article in Thieme ConnectPubMed
  • 65 Ni P, Tan J, Li R, Huang H, Zhang F, Deng G.-J. RSC Adv. 2020; 10: 3931
    CrossrefPubMed
  • 66 Jonaghani MZ, Zali-Boeini H, Taheri R, Rudbari HA, Askari B. RSC Adv. 2016; 6: 34940
    Crossref
  • 67 Li G, Xie H, Chen J, Guo Y, Deng G.-J. Green Chem. 2017; 19: 4043
    Crossref
  • 68 Che X, Jiang J, Xiao F, Huang H, Deng GJ. Org. Lett. 2017; 19: 4576
    CrossrefPubMed
  • 69 Singh M, Awasthi P, Singh V. Eur. J. Org. Chem. 2020; 1023
    CrossrefPubMed
    • 70a Dang P, Zheng Z, Liang Y. J. Org. Chem. 2017; 82: 2263
      CrossrefPubMed
    • 70b Zhang X, Zeng W, Yang Y, Huang H, Liang Y. Org. Lett. 2014; 16: 876
      CrossrefPubMed
  • 71 Zhu X, Yang Y, Xiao G, Song J, Liang Y, Deng G. Chem. Commun. 2017; 53: 11917
    CrossrefPubMed
  • 72 Jiang J, Li G, Zhang F, Xie H, Deng G.-J. Adv. Synth. Catal. 2018; 360: 1622
    CrossrefPubMed
  • 73 Liu Y, Yuan X, Guo X, Zhang X, Chen B. Tetrahedron 2018; 74: 6057
    CrossrefPubMed
  • 74 Zhang J, Zhao X, Liu P, Sun P. J. Org. Chem. 2019; 84: 12596
    CrossrefPubMed
    • 75a Wang HM, Cao XX, Xiao FH, Liu SW, Deng GJ. Org. Lett. 2013; 15: 4900
      CrossrefPubMed
    • 75b Wu M, Hu X, Liu J, Liao Y, Deng GJ. Org. Lett. 2012; 14: 2722
      CrossrefPubMed
  • 76 Xing Q, Ma Y, Xie H, Xiao F, Zhang F, Deng GJ. J. Org. Chem. 2019; 84: 1238
    CrossrefPubMed
    • 77a Chen J, Chang D, Xiao F, Deng G.-j. Prog. Chem. 2018; 30: 564
    • 77b Girard SA, Huang H, Zhou F, Deng G.-J, Li C.-J. Org. Chem. Front. 2015; 2: 279
      Crossref
  • 78 Xu Z, Huang H, Chen H, Deng G.-J. Org. Chem. Front. 2019; 6: 3060
    Crossref
  • 79 Wang Z, Xie H, Xiao F, Guo Y, Huang H, Deng G.-J. Eur. J. Org. Chem. 2017; 1604
    • 80a Chen J, Jiang Y, Yu JT, Cheng J. J. Org. Chem. 2016; 81: 271
      CrossrefPubMed
    • 80b Zhou Z, Liu Y, Chen J, Yao E, Cheng J. Org. Lett. 2016; 18: 5268
      CrossrefPubMed
  • 81 Zhou Z, Liu M, Sun S, Yao E, Liu S, Wu Z, Yu J.-T, Jiang Y, Cheng J. Tetrahedron Lett. 2017; 58: 2571
    Crossref
  • 82 Yang Z, Liang Y, Li A, Liu K, Li L, Yang T, Zhou C. J. Org. Chem. 2019; 84: 16262
    CrossrefPubMed
  • 83 Ishikawa T, Kimura M, Kumoi T, Iida H. ACS Catal. 2017; 7: 4986
    Crossref
  • 84 Li W, He J, Liu P, Zhang J, Dai B. ChemistrySelect 2019; 4: 10587
    Crossref
  • 85 Mo SK, Teng QH, Pan YM, Tang HT. Adv. Synth. Catal. 2019; 361: 1756
    Crossref
  • 86 Nguyen TB, Retailleau P. Org. Lett. 2017; 19: 3879
    CrossrefPubMed
  • 87 Guo JR, Gong JF, Song MP. Org. Biomol. Chem. 2019; 17: 5029
    CrossrefPubMed
  • 88 Zhang J, Song C, Sheng L, Liu P, Sun P. J. Org. Chem. 2019; 84: 2191
    CrossrefPubMed
  • 89 Nguyen TB, Retailleau P. Org. Lett. 2019; 21: 279
    CrossrefPubMed
  • 90 Jiang J, Tuo X, Fu Z, Huang H, Deng GJ. Org. Biomol. Chem. 2020; 18: 3234
    CrossrefPubMed
  • 91 Chen Q, Xie R, Jia H, Sun J, Lu G, Jiang H, Zhang M. J. Org. Chem. 2020; 85: 5629
    CrossrefPubMed