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Synthesis 2020; 52(17): 2541-2550
DOI: 10.1055/s-0040-1707120
paper
© Georg Thieme Verlag Stuttgart · New York

Sulfite-Promoted C–H Fluoroalkyl Sulfuration of Imidazoheterocycles with Bromofluoroacetate and Elemental Sulfur

Yong-Chao Gao
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn
,
Zi-Hao Huang
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn
,
Zhao-Sheng Zhang
b   State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: ziningcui@scau.edu.cn
,
Jin-Xin Xie
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn
,
Zi-Ning Cui∗
b   State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: ziningcui@scau.edu.cn
c   Lingnan Guangdong Laboratory of Modern Agriculture, Guangzhou 510642, P. R. of China
,
Ri-Yuan Tang  ∗
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn
c   Lingnan Guangdong Laboratory of Modern Agriculture, Guangzhou 510642, P. R. of China
› Author AffiliationsWe gratefully thank the Guangdong Basic and Applied Basic Research Foundation (Grant No. 2019B151502052) for financial support.
Further Information

Publication History

Received: 05 March 2020

Accepted after revision: 22 April 2020

Publication Date:
18 May 2020 (online)

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Abstract

A transition-metal-free sulfite-promoted three-component C–H sulfuration between imidazoheterocycles, elemental sulfur, and bromofluoroacetate is developed. Sulfites, including Na2S2O4, NaHSO3, and Na2S2O3, are able to promote the formation of two C–S bonds in one step using elemental sulfur as a green sulfurating agent, allowing the rapid introduction of the synthetically useful S-fluoroacetate group into imidazoheterocycles. These new imidazoheterocycle derivatives bearing an S-fluoroacetate group can be easily modified to produce pharmaceutically attractive compounds.

Key words

sulfites - sulfides - elemental sulfur - C–H functionalization - imidazoles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707120.
  • Supporting Information
 

  • References

    • 1a Mellah M, Voituriez A, Schulz E. Chem. Rev. 2007; 107: 5133
      CrossrefPubMed
    • 1b Landelle G, Panossian A, Leroux FR. Curr. Top. Med. Chem. 2014; 14: 941
      CrossrefPubMed
    • 1c Feng M, Tang B, Liang SH, Jiang X. Curr. Top. Med. Chem. 2016; 16: 1200
      CrossrefPubMed
    • 1d Zhao J, Jiang X. Chin. Chem. Lett. 2018; 29: 1079
      CrossrefPubMed
    • 1e Wang N, Saidhareddy P, Jiang X. Nat. Prod. Rep. 2020; 37: 246
      CrossrefPubMed
    • 2a Jarrett JT. J. Biol. Chem. 2015; 290: 3972
      CrossrefPubMed
    • 2b Konaklieva MI, Plotkin BJ. Recent Pat. Anti-Infect. Drug Discovery 2006; 1: 177
      PubMed
    • 2c Zysman-Colman E, Leste-Lassere P, Harpp DN. J. Sulfur Chem. 2008; 29: 309

      For reviews on the construction of C–S bonds, see:
    • 3a Ghaderi A. Tetrahedron 2016; 72: 4758 ; and references cited therein
      Crossref
    • 3b Qiao Z, Jiang X. Org. Biomol. Chem. 2017; 15: 1942
      CrossrefPubMed
    • 3c Shen C, Zhang P, Sun Q, Bai S, Hor TS. A, Liu X. Chem. Soc. Rev. 2015; 44: 291
      CrossrefPubMed
    • 4a Nguyen BT. Adv. Synth. Catal. 2017; 359: 1066 ; and references cited therein
      Crossref
    • 4b Meyer B. Chem. Rev. 1976; 76: 367
      Crossref
    • 5a Chen F.-J, Liao G, Li X, Wu J, Shi B.-F. Org. Lett. 2014; 16: 5644
      CrossrefPubMed
    • 5b Han R, Hillhouse GL. J. Am. Chem. Soc. 1998; 120: 7657
      Crossref
    • 5c Chen C, Chu L, Qing F.-L. J. Am. Chem. Soc. 2012; 134: 12454
      CrossrefPubMed
    • 5d Zhou Z, Liu Y, Chen J, Yao E, Cheng J. Org. Lett. 2016; 18: 5268
      CrossrefPubMed
    • 5e Chen C, Xie Y, Chu L, Wang R.-W, Zhang X, Qing F.-L. Angew. Chem. Int. Ed. 2012; 51: 2492
      CrossrefPubMed
    • 5f Shibahara F, Kanai T, Yamaguchi E, Kamei A, Yamauchi T, Murai T. Chem. Asian J. 2014; 9: 237
      CrossrefPubMed
    • 5g Zhang G, Yi H, Chen H, Bian C, Liu C, Lei A. Org. Lett. 2014; 16: 6156
      CrossrefPubMed
    • 5h Wang Z, Wang Y, Zhang W.-X, Hou Z, Xi Z. J. Am. Chem. Soc. 2009; 131: 15108
      CrossrefPubMed
    • 5i Nguyen TB, Ermolenko L, Al-Mourabit A. Org. Lett. 2013; 15: 4218
      CrossrefPubMed
    • 5j Wang M, Fan Q, Jiang X. Org. Lett. 2016; 18: 5756
      CrossrefPubMed
    • 5k Feng C, Peng Y, Ding G, Li X, Cui C, Yan Y. Chem. Commun. 2018; 54: 13367
      CrossrefPubMed
    • 5l Liu Z, Gao R, Lou J, He Y, Yu Z. Adv. Synth. Catal. 2018; 360: 3097
      CrossrefPubMed
    • 6a Siva Reddy A, Kumara Swamy KC. Org. Lett. 2015; 17: 2996
      CrossrefPubMed
    • 6b Arisawa M, Ichikawa T, Yamaguchi M. Org. Lett. 2012; 14: 5318
      CrossrefPubMed
    • 6c Huang Y, He X, Lin X, Rong M, Weng Z. Org. Lett. 2014; 16: 3284
      CrossrefPubMed
    • 6d Weng Z, He W, Chen C, Lee R, Tan D, Lai Z, Kong D, Yuan Y, Huang K.-W. Angew. Chem. Int. Ed. 2013; 52: 1548
      CrossrefPubMed
    • 6e Paul R, Punniyamurthy T. RSC Adv. 2012; 2: 7057
      Crossref
    • 6f Xiao F, Chen S, Li C, Huang H, Deng G.-J. Adv. Synth. Catal. 2016; 358: 3881
      Crossref

      For recent references on the sulfuration of indoles using elemental sulfur, see:
    • 7a Liao Y, Peng Y, Qi H, Deng G.-J, Gong H, Li C.-J. Chem. Commun. 2015; 51: 1031
      CrossrefPubMed
    • 7b Liu J, Yan X, Liu N, Zhang Y, Zhao S, Wang X, Zhuo K, Yue Y. Org. Chem. Front. 2018; 5: 1034
      Crossref
    • 7c Liu J, Zhang Y, Yue Y, Wang Z, Shao H, Zhuo K, Lv Q, Zhang Z. J. Org. Chem. 2019; 84: 12946
      CrossrefPubMed
    • 7d Lu C, Huang H, Tuo X, Jiang P, Zhang F, Deng G.-J. Org. Chem. Front. 2019; 6: 2738
      Crossref
    • 7e Thomas J, Jana S, Sonawane M, Fiey B, Balzarini J, Liekens S, Dehaen W. Org. Biomol. Chem. 2017; 15: 3892
      CrossrefPubMed

      For recent references on the sulfuration of imidazoheterocycles using elemental sulfur, see:
    • 8a Li J, Li C, Yang S, An Y, Wu W, Jiang H. J. Org. Chem. 2016; 81: 7771
      CrossrefPubMed
    • 8b Ravi C, Reddy NN. K, Pappula V, Samanta S, Adimurthy S. J. Org. Chem. 2016; 81: 9964
      CrossrefPubMed
    • 8c Shi S, Chen J, Zhuo S, Wu Z, Fang M, Tang G, Zhao Y. Adv. Synth. Catal. 2019; 361: 3210
      Crossref
    • 8d Wu W, Ding Y, Xie P, Tang Q, Pittman CU. Jr, Zhou A. Tetrahedron 2017; 73: 2151
      Crossref
    • 8e Zhu W, Ding Y, Bian Z, Xie P, Xu B, Tang Q, Wu W, Zhou A. Adv. Synth. Catal. 2017; 359: 2215
      Crossref

      For our publications on the sulfuration of imidazoheterocycles using elemental sulfur, see:
    • 9a Zhang J.-R, Liao Y.-Y, Deng J.-C, Feng K.-Y, Zhang M, Ning Y.-Y, Lin Z.-W, Tang R.-Y. Chem. Commun. 2017; 53: 7784
      CrossrefPubMed
    • 9b Zhang J.-R, Zhan L.-Z, Wei L, Ning Y.-Y, Zhong X.-L, Lai J.-X, Xu L, Tang R.-Y. Adv. Synth. Catal. 2018; 360: 533
      Crossref
    • 9c Gao Y.-C, Huang Z.-B, Xu L, Li Z.-D, Lai Z.-S, Tang R.-Y. Org. Biomol. Chem. 2019; 17: 2279
      CrossrefPubMed
    • 9d Deng J.-C, Zhang J.-C, Li M.-H, Huang J.-C, Lai Z.-S, Tong X.-Y, Cui Z.-N, Tang R.-Y. Org. Biomol. Chem. 2019; 17: 7854
      CrossrefPubMed
    • 9e Deng J.-C, Zhuang S.-B, Liu Q.-Z, Lin Z.-W, Su Y.-L, Chen J.-H, Tang R.-Y. RSC Adv. 2017; 7: 54013
      Crossref
    • 10a Enguehard-Gueiffier C, Gueiffier A. Mini-Rev. Med. Chem. 2007; 7: 888
      CrossrefPubMed
    • 10b Couty F, Evano G. In Comprehensive Heterocyclic Chemistry III, Vol. 11. Katritzky AR, Rees CW. Pergamon; Oxford: 2008: 409
      Google Scholar
    • 10c Koubachi J, Kazzouli SE, Bousmina M, Guillaumet G. Eur. J. Org. Chem. 2014; 5119 ; and references cited therein
  • 11 Ilardi EA, Vitaku E, Njardarson JT. J. Med. Chem. 2014; 57: 2832
    CrossrefPubMed
    • 12a Deng J.-C, Gao Y.-C, Zhu Z, Xu L, Li Z.-D, Tang R.-Y. Org. Lett. 2019; 21: 545
      CrossrefPubMed
    • 12b Deng J.-C, Chen J.-H, Zhang J.-R, Lu T.-T, Tang R.-Y. Adv. Synth. Catal. 2018; 360: 4795
      Crossref
    • 13a Jiao J, Wei L, Ji X.-M, Hu M.-L, Tang R.-Y. Adv. Synth. Catal. 2016; 358: 268
      Crossref
    • 13b Wei L, Deng J.-C, Zhuo B.-L, Xu L, Tang R.-Y. ChemistrySelect 2016; 1: 6293
      Crossref
    • 13c Wei L, Xu L, Tang R.-Y. RSC Adv. 2015; 5: 107927
      Crossref
    • 13d Ji X.-M, Zhu S.-J, Chen F, Zhang X.-G, Tang R.-Y. Synthesis 2015; 47: 659
      Article in Thieme Connect
    • 13e Huang Z.-H, Xia X.-J, Huang Z.-H, Xu L, Zhang X.-Y, Tang R.-Y. Org. Biomol. Chem. 2020; 18: 1369
      CrossrefPubMed
    • 14a Xiao X, Feng M, Jiang X. Chem. Commun. 2015; 51: 4208
      CrossrefPubMed
    • 14b Zhang Y, Li Y, Zhang X, Jiang X. Chem. Commun. 2015; 51: 941
      CrossrefPubMed
  • 15 Douha A, Amat-Guerri F, Acuna AU. J. Phys. Chem. 1995; 99: 76
    Crossref
    • 16a Kazzouli SE, Bellay AG, Berteina-Raboin S, Delagrange P, Caignard D.-H, Guillaumet G. Eur. J. Med. Chem. 2011; 46: 4252
      CrossrefPubMed
    • 16b Trapani G, Franco M, Ricciardi L, Latrofa A, Genchi G, Sanna E, Tuveri F, Cagetti E, Biggio G, Liso G. J. Med. Chem. 1997; 40: 3109
      CrossrefPubMed
    • 17a Zhang C.-P, Chen Q.-Y, Guo Y, Xiao J.-C, Gu Y.-C. Chem. Soc. Rev. 2012; 41: 4536
      CrossrefPubMed
    • 17b Huang B.-N, Huang W.-Y, Hu C.-M. Acta Chim. Sinica 1981; 39: 481
    • 18a Fu W, Song Q. Org. Lett. 2018; 20: 393
      CrossrefPubMed
    • 18b Ouyang X.-H, Song R.-J, Li J.-H. Chem. Asian J. 2018; 13: 2316
      CrossrefPubMed
    • 18c Chen J.-H, Wasim A, Li M.-H, Li Z.-D, Cui Z.-N, Tang R.-Y. Adv. Synth. Catal. 2020; 362: 269
      Crossref
    • 19a Li Y, Xie W, Jiang X. Chem. Eur. J. 2015; 21: 16059
      CrossrefPubMed
    • 19b Li Y, Pu J, Jiang X. Org. Lett. 2014; 16: 2692
      CrossrefPubMed
    • 19c Qiao Z, Wei J, Jiang X. Org. Lett. 2014; 16: 1212
      CrossrefPubMed
    • 19d Liu H, Jiang X. Pure Appl. Chem. 2014; 86: 307
      Crossref
    • 19e Qiao Z, Liu H, Xiao X, Fu Y, Wei J, Li Y, Jiang X. Org. Lett. 2013; 15: 2594
      CrossrefPubMed