Download PDF
Synthesis 2022; 54(01): 67-78
DOI: 10.1055/a-1578-2911
short review

Recent Advances on Annulation Reactions with Allyl and Propargyl Sulfonium Salts

Qing-Zhu Li
,
Wen-Lin Zou
,
Zhi-Qiang Jia
,
Jun-Long Li  ∗
Financial support from the National Natural Science Foundation of China (NSFC) (22071011 and 21871031), the Long-quan Talents Program, the Science and Technology Department of Sichuan Province (2021YJ0404), and the Innovative Project of Chengdu University is gratefully acknowledged.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

Allyl and propargyl sulfonium salts are readily available reagents that have recently emerged as versatile building blocks for the assembly of cyclic skeletons. As an alternative to classical sulfonium salts, allyl and propargyl sulfonium salts can be converted into the corresponding vinyl sulfur ylide or allenic sulfonium salt intermediates that contain diverse nucleophilic or electrophilic reactive positions, thereby enabling a great variety of annulation reactions. In this short review, we provide a comprehensive overview of the recent developments in this growing field by summarizing annulation reactions involving allyl and propargyl sulfonium salts.

1 Introduction

2 Annulations with Allyl Sulfonium Salts

3 Annulations with Propargyl Sulfonium Salts

4 Conclusion

Key words

allyl sulfonium salts - propargyl sulfonium salts - sulfur ylides - allenyl sulfonium salts - annulation reactions


Publication History

Received: 07 July 2021

Accepted after revision: 04 August 2021

Accepted Manuscript online:
04 August 2021

Article published online:
30 August 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Johnson AW, LaCount RB. J. Am. Chem. Soc. 1961; 83: 417
      CrossrefPubMed
    • 1b Corey EJ, Chaykovsky M. J. Am. Chem. Soc. 1965; 87: 1353
      CrossrefPubMed
  • 2 Kaiser D, Klose I, Oost R, Neuhaus J, Maulide N. Chem. Rev. 2019; 119: 8701
    CrossrefPubMed

      • For selected reviews on transformations with sulfur ylides, see:
    • 3a Lu L.-Q, Li T.-R, Wang Q, Xiao W.-J. Chem. Soc. Rev. 2017; 46: 4135
      CrossrefPubMed
    • 3b Neuhaus JD, Oost R, Merad J, Maulide N. Top. Curr. Chem. 2018; 376: 15
      CrossrefPubMed
    • 3c Burtoloso AC. B, Dias RM. P, Leonarczyk IA. Eur. J. Org. Chem. 2013; 5005
      Crossref
    • 3d Zhang Y, Wang J. Coord. Chem. Rev. 2010; 254: 941
      CrossrefPubMed

      For selected reviews on ylide [2+1] annulations, see:
    • 4a Sun X.-L, Tang Y. Acc. Chem. Res. 2008; 41: 937
      CrossrefPubMed
    • 4b Lebel H, Marcoux J.-F, Molinaro C, Charette AB. Chem. Rev. 2003; 103: 977
      CrossrefPubMed
    • 4c Li A.-H, Dai L.-X, Aggarwal VK. Chem. Rev. 1997; 97: 2341
      CrossrefPubMed

      • For selected examples, see:
    • 4d Aggarwal VK, Alonso E, Hynd G, Lydon KM, Palmer MJ, Porcelloni M, Studley JR. Angew. Chem. Int. Ed. 2001; 40: 1430
      CrossrefPubMed
    • 4e Deng X.-M, Cai P, Ye S, Sun X.-L, Liao W.-W, Li K, Tang Y, Wu Y.-D, Dai L.-X. J. Am. Chem. Soc. 2006; 128: 9730
      CrossrefPubMed
    • 4f Illa O, Arshad M, Ros A, McGarrigle EM, Aggarwal VK. J. Am. Chem. Soc. 2010; 132: 1828
      Article in Thieme ConnectPubMed
    • 4g Li Q.-Z, Zhang X, Zeng R, Dai Q.-S, Liu Y, Shen X.-D, Leng H.-J, Yang K.-C, Li J.-L. Org. Lett. 2018; 20: 3700
      CrossrefPubMed
    • 4h Li Q.-Z, Zhang X, Xie K, Dai Q.-S, Zeng R, Liu Y.-Q, Jia Z.-Q, Feng X, Li J.-L. Green Chem. 2019; 21: 2375
      Crossref
    • 4i Hock KJ, Hommelsheim R, Mertens L, Ho J, Nguyen TV, Koenigs RM. J. Org. Chem. 2017; 82: 8220
      CrossrefPubMed
    • 4j Zhang X, Zeng R, Feng X, Dai Q.-S, Liu Y, Liu Y.-Q, Wang Q.-W, Li Q.-Z, Li J.-L. Asian J. Org. Chem. 2018; 7: 2065
      CrossrefPubMed
    • 4k Lee J, Ko D, Park H, Yoo EJ. Chem. Sci. 2020; 11: 1672
      CrossrefPubMed

      For selected reviews on ylide [4+1] annulations, see:
    • 5a Zhu C, Ding Y, Ye L.-W. Org. Biomol. Chem. 2015; 13: 2530
      CrossrefPubMed
    • 5b Chen J.-R, Hu X.-Q, Lu L.-Q, Xiao W.-J. Chem. Rev. 2015; 115: 5301
      CrossrefPubMed

      • For selected recent examples, see:
    • 5c Wang Q, Li T.-R, Lu L.-Q, Li M.-M, Zhang K, Xiao W.-J. J. Am. Chem. Soc. 2016; 138: 8360
      CrossrefPubMed
    • 5d Wang Q, Qi X, Lu L.-Q, Li T.-R, Yuan Z.-G, Zhang K, Li B.-J, Lan Y, Xiao W.-J. Angew. Chem. Int. Ed. 2016; 55: 2840
      CrossrefPubMed
    • 5e Liu Y.-Y, Yu X.-Y, Chen J.-R, Qiao M.-M, Qi X, Shi D.-Q, Xiao W.-J. Angew. Chem. Int. Ed. 2017; 56: 9527
      CrossrefPubMed
    • 5f Liu Y.-Q, Li Q.-Z, Zhu H.-P, Feng X, Peng C, Huang W, Li J.-L, Han B. J. Org. Chem. 2018; 83: 12753
      CrossrefPubMed

      For [3+1] annulations with sulfur ylides, see:
    • 6a Li C, Jiang K, Ouyang Q, Liu T.-Y, Chen Y.-C. Org. Lett. 2016; 18: 2738
      CrossrefPubMed
    • 6b Deng Y, Massey LA, Zavalij PY, Doyle MP. Angew. Chem. Int. Ed. 2017; 56: 7479
      CrossrefPubMed
    • 6c Leng H.-J, Li Q.-Z, Xiang P, Qi T, Dai Q.-S, Jia Z.-Q, Gou C, Zhang X, Li J.-L. Org. Lett. 2021; 23: 1451
      CrossrefPubMed
  • 7 Li Q.-Z, Jia Z.-Q, Chen L, Zhang X, Leng H.-J, Zeng R, Liu Y.-Q, Zou W.-L, Li J.-L. Org. Lett. 2021; 23: 814
    CrossrefPubMed

      • For selected books and reviews on annulation reactions, see:
    • 8a Ma S.-M. Handbook of Cyclization Reactions . Wiley-VCH; New York: 2010
      CrossrefGoogle Scholar
    • 8b Methods and Applications of Cycloaddition Reactions in Organic Synthesis. Nishiwaki N. John Wiley & Sons; New York: 2014
      CrossrefGoogle Scholar
    • 8c Han B, He X.-H, Liu Y.-Q, He G, Peng C, Li J.-L. Chem. Soc. Rev. 2021; 50: 1522
      CrossrefPubMed

      • For selected examples of our contributions on cyclization reactions, see:
    • 8d Li Q, Zhou L, Shen X.-D, Yang K.-C, Zhang X, Dai Q.-S, Leng H.-J, Li Q.-Z, Li J.-L. Angew. Chem. Int. Ed. 2018; 57: 1913
      CrossrefPubMed
    • 8e Zeng R, Li J.-L, Zhang X, Liu Y.-Q, Jia Z.-Q, Leng H.-J, Huang Q.-W, Liu Y, Li Q.-Z. ACS Catal. 2019; 9: 8256
      Crossref

      For selected reviews, see:
    • 9a Pulis AP, Procter DJ. Angew. Chem. Int. Ed. 2016; 55: 9842
      CrossrefPubMed
    • 9b Yanagi T, Nogi K, Yorimitsu H. Tetrahedron Lett. 2018; 59: 2951
      Crossref
    • 9c Huang X, Klimczyk S, Maulide N. Synthesis 2012; 44: 175

      • For selected examples, see:
    • 9d Yan J, Pulis AP, Perry GJ. P, Procter DJ. Angew. Chem. Int. Ed. 2019; 58: 15675
      CrossrefPubMed
    • 9e He Z, Shrives HJ, Fernández-Salas JA, Abengózar A, Neufeld J, Yang K, Pulis AP, Procter DJ. Angew. Chem. Int. Ed. 2018; 57: 5759
      CrossrefPubMed
    • 9f Shrives HJ, Fernández-Salas JA, Hedtke C, Pulis AP, Procter DJ. Nat. Commun. 2017; 8: 14801
      CrossrefPubMed
    • 9g Hu G, Xu J, Li P. Org. Lett. 2014; 16: 6036
      CrossrefPubMed
    • 9h Akai S, Kawashita N, Wada Y, Satoh H, Alinejad AH, Kakiguchi K, Kuriwaki I, Kita Y. Tetrahedron Lett. 2006; 47: 1881
      Crossref

      For selected examples, see:
    • 10a Zhu B.-H, Zheng J.-C, Yu C.-B, Sun X.-L, Zhou Y.-G, Shen Q, Tang Y. Org. Lett. 2010; 12: 504
      CrossrefPubMed
    • 10b Roy S, Piradhi V. ChemistrySelect 2017; 2: 6159
      Crossref
  • 11 Wang Q.-G, Deng X.-M, Zhu B.-H, Ye L.-W, Sun X.-L, Li C.-Y, Zhu C.-Y, Shen Q, Tang Y. J. Am. Chem. Soc. 2008; 130: 5408
    CrossrefPubMed
  • 12 Zhu B.-H, Zhou R, Zheng J.-C, Deng X.-M, Sun X.-L, Shen Q, Tang Y. J. Org. Chem. 2010; 75: 3454
    CrossrefPubMed
  • 13 Jia P, Huang Y. Org. Lett. 2016; 18: 2475
    Article in Thieme ConnectPubMed
  • 14 Wang C, Zhang J, Wang Z, Hui X.-P. Org. Chem. Front. 2020; 7: 1469
    CrossrefPubMed
  • 15 Chen Z, Zhang J. Chem. Asian J. 2009; 4: 1527
    CrossrefPubMed
  • 16 Meng Z, Wang Q, Lu D, Yue T, Ai P, Liu H, Yang W, Zheng J. J. Org. Chem. 2020; 85: 15026
    CrossrefPubMed
  • 17 Gao F, Huang Y. Adv. Synth. Catal. 2014; 356: 2422
    CrossrefPubMed
  • 18 Satham L, Namboothiri IN. N. J. Org. Chem. 2018; 83: 9471
    CrossrefPubMed
  • 19 Parameshwar M, Singam MK. R, Nagireddy A, Nanubolu JB, Reddy MS. Chem. Commun. 2020; 56: 13457
    CrossrefPubMed
  • 20 Zhang Y, Yu A, Jia J, Ma S, Li K, Wei Y, Meng X. Chem. Commun. 2017; 53: 10672
    CrossrefPubMed
  • 21 Wang D, Wang X, Zhang X, Miao Z. Synthesis 2019; 51: 2149
    Crossref
  • 22 Chen Q, Pan Y, Zhao D, Yang W, Zheng J. RSC Adv. 2020; 10: 21895
    CrossrefPubMed
  • 23 Fei X.-H, Zhao Y.-L, Yang F.-F, Guan X, Li Z.-Q, Wang D.-P, Zhou M, Yang Y.-Y, He B. Adv. Synth. Catal. 2021; 363: 3018
    CrossrefPubMed
  • 24 Li J.-L, Dai Q.-S, Yang K.-C, Liu Y, Zhang X, Leng H.-J, Peng C, Huang W, Li Q.-Z. Org. Lett. 2018; 20: 7628
    CrossrefPubMed
  • 25 Chen J, Jia P, Huang Y. Org. Lett. 2018; 20: 6715
    CrossrefPubMed
  • 26 Yin W, Fang L, Wang Z, Gao F, Li Z, Wang Z. Org. Lett. 2019; 21: 7361
    CrossrefPubMed
  • 27 Ding W, Zhang Y, Yu A, Zhang L, Meng X. J. Org. Chem. 2018; 83: 13821
    CrossrefPubMed
  • 28 Appleyard GD, Stirling CJ. M. J. Chem. Soc. C 1969; 1904
    Crossref
  • 29 Batty JW, Howes PD, Stirling CJ. M. J. Chem. Soc., Perkin Trans. 1 1973; 65
    CrossrefPubMed
    • 30a Aso M, Ojida A, Yang G, Cha OJ, Osawa E, Kanematsu K. J. Org. Chem. 1993; 58: 3960
      Crossref
    • 30b Ojida A, Tanoue F, Kanematsu K. J. Org. Chem. 1994; 59: 5970
      Crossref
  • 31 Jia P, Zhang Q, Jin H, Huang Y. Org. Lett. 2017; 19: 412
    CrossrefPubMed
  • 32 Jia P, Zhang Q, Ou Q, Huang Y. Org. Lett. 2017; 19: 4664
    CrossrefPubMed
  • 33 Jia P, Zhang Q, Zhuge Y, Liwei X, Huang Y. Adv. Synth. Catal. 2018; 360: 438
    Crossref
  • 34 Lu T, Zhang X, Miao Z. Org. Biomol. Chem. 2020; 18: 3303
    CrossrefPubMed
  • 35 Jia T, Zeng G, Zhang C, Zeng L, Zheng W, Li S, Wu K, Shao J, Zhang J, Zhu H. Chem. Commun. 2021; 57: 2657
    CrossrefPubMed
  • 36 Shen S, Yang Y, Duan J, Jia Z, Liang J. Org. Biomol. Chem. 2018; 16: 1068
    CrossrefPubMed
  • 37 Deng B, Rao CB, Zhang R, Li J, Liang Y, Zhao Y, Gao M, Dong D. Adv. Synth. Catal. 2019; 361: 4549
    Crossref
  • 38 Chen Q, Pan Y, Yue T, Yang W, Liu H, Zheng J. Org. Lett. 2020; 22: 6096
    CrossrefPubMed
  • 39 Jia P, Huang Y. Adv. Synth. Catal. 2018; 360: 3044
    Crossref
  • 40 Zhou Y, Chen Y, Huang Y. Org. Lett. 2020; 22: 5941
    CrossrefPubMed