Download PDF
CC BY-NC-ND 4.0 · SynOpen 2021; 05(03): 232-251
DOI: 10.1055/a-1577-9755
review

The Renaissance of Alkali Metabisulfites as SO2 Surrogates

Ashish Kumar Sahoo
,
Anjali Dahiya
,
Amitava Rakshit
,
Bhisma K. Patel  ∗
B.K.P. acknowledges the support of this research by the Department of Science and Technology, Science and Engineering Research Board, India (DST/SERB; EMR/2016/007042) and the Council of Scientific and Industrial Research, India (CSIR; 02(0365)/19/EMR-II). A.K.S., A.D., and A.R. thank IIT Guwahati for Fellowships and for providing necessary facilities.
› Further Information
   Permissions and Reprints All articles of this category


Abstract

The upsurge of interest in the development of methodologies for the construction of sulfur-containing compounds via the use of expedient reagents has established sustainable tools in organic chemistry. This review focuses on sulfonylation reactions using inorganic sulfites (Na2S2O5 or K2S2O5) as the sulfur dioxide surrogates. Compared to the bis-adduct with DABCO, which is an excellent surrogate of gaseous SO2, the use of sodium or potassium metabisulfites as SO2 surrogates are equally efficient. The objective of the current review is to exemplify recent sulfonylation reactions using inorganic sulfites. For better understanding, the review is categorized according to the mode of reactions: transition-metal-catalyzed SO2 insertion, metal-free SO2 insertion, and visible-light-mediated SO2 insertion. All the reactions in each of the sections are illustrated with selected examples with a pertinent explanation of the proposed mechanism.

1 Introduction

2 Outlines of the Reactions Involving SO2 Insertion

2.1 Transition-Metal-Catalyzed SO2 Insertion

2.2 Transition-Metal-Free SO2 Insertion

2.3 Visible-Light-Mediated SO2 Insertion

3 Conclusion and Outlook

Key words

DABCO·(SO2)2 - sodium or potassium metabisulfite - SO2 surrogate - sulfonylation reaction - SO2 insertion


Publication History

Received: 08 July 2021

Accepted after revision: 03 August 2021

Accepted Manuscript online:
03 August 2021

Article published online:
26 August 2021

© 2021. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Bartholow M. Pharmacy Times 2011; 48
  • 2 Drews J. Science 2000; 287: 1960
    CrossrefPubMed
  • 3 EI-Awa A, Noshi MN, du Jourdin XM, Fuchs PL. Chem. Rev. 2009; 109: 2315
    CrossrefPubMed
  • 4 Ahmad I. Shagufta Int. J. Pharm. Pharm. Sci. 2015; 7: 19
    CrossrefPubMed
  • 5 Trost BM, Kalnmals CA. Chem. Eur. J. 2019; 25: 11193
    CrossrefPubMed
  • 6 Liu X, Cong T, Liu P, Sun P. Org. Biomol. Chem. 2016; 14: 9416
    CrossrefPubMed
  • 7 Sun K, Chen X.-L, Li X, Qu L.-B, Bi W.-Z, Chen X, Ma H.-L, Zhang S.-T, Han B.-W, Zhao Y.-F, Li C.-J. Chem. Commun. 2015; 51: 12111
    CrossrefPubMed
  • 8 Liang H, Jiang K, Ding W, Yuan Y, Shuai L, Chen Y, Wei Y. Chem. Commun. 2015; 51: 16928
    CrossrefPubMed
  • 9 Zhao X, Dimitrijevic E, Dong VM. J. Am. Chem. Soc. 2009; 131: 3466
    CrossrefPubMed
  • 10 Chen ZZ, Liu S, Hao W.-J, Xu G, Wu S, Miao J.-N, Jiang B, Wang S.-L, Tu S.-J, Li G. Chem. Sci. 2015; 6: 6654
    CrossrefPubMed
  • 11 Yang Y, Bao Y, Guan Q, Sun Q, Zha Z, Wang Z. Green Chem. 2017; 19: 112
    Crossref
  • 12 Khakyzadeh V, Wang Y, Breit B. Chem. Commun. 2017; 53: 4966
    CrossrefPubMed
  • 13 Wang Y, Ma L, Ma M, Zheng H, Shao Y, Wan X. Org. Lett. 2016; 18: 5082
    CrossrefPubMed
  • 14 Tang X, Huang L, Xu Y, Yang J, Wu W, Jiang H. Angew. Chem. Int. Ed. 2014; 53: 4205
    CrossrefPubMed
  • 15 Xu Y, Zhao J, Tang X, Wu W, Jiang H. Adv. Synth. Catal. 2014; 356: 2029
    Crossref
  • 16 Wu W, Yi S, Yu Y, Huang W, Jiang H. J. Org. Chem. 2017; 82: 1224
    CrossrefPubMed
  • 17 Nguyen B, Emmet EJ, Willis MC. J. Am. Chem. Soc. 2010; 132: 16372
    CrossrefPubMed
  • 18 Santos PS, Mello MT. S. J. Mol. Struct. 1988; 178: 121
    Crossref
  • 19 Qiu G, Zhou K, Gao L, Wu J. Org. Chem. Front. 2018; 5: 691
    Crossref
  • 20 Ye S, Yang M, Wu J. Chem. Commun. 2020; 56: 4145
    CrossrefPubMed
  • 21 Liu J, Zheng L. Adv. Synth. Catal. 2019; 361: 1710
    Crossref
  • 22 Ye S, Qiu G, Wu J. Chem. Commun. 2019; 55: 1013
    CrossrefPubMed
  • 23 Ye S, Li X, Xie W, Wu J. Eur. J. Org. Chem. 2020; 1274
    Crossref
  • 24 Feng M, Tang B, Liang SH, Jiang X. Curr. Top. Med. Chem. 2016; 16: 1200
    CrossrefPubMed
  • 25 Wang X, Yang M, Kuang Y, Liu J.-B, Fan X, Wu J. Chem. Commun. 2020; 56: 3437
    CrossrefPubMed
  • 26 Ye S, Wu J. Chem. Commun. 2012; 48: 10037
    CrossrefPubMed
  • 27 Marset X, Torregrosa-Crespo J, Martinez-Espinosa R, Guillena G, Ramon DJ. Green Chem. 2019; 21: 4127
    Crossref
  • 28 Konishi H, Tanaka H, Manabe K. Org. Lett. 2017; 19: 1578
    CrossrefPubMed
  • 29 Meng Y, Wang M, Jiang X. Angew. Chem. Int. Ed. 2020; 59: 1346
    CrossrefPubMed
  • 30 Giannetti AM, Wong H, Dijkgraaf GJ. P, Dueber EC, Ortwine DF, Bravo BJ, Gould SE, Plise EG, Lum BL, Malhi V, Graham RA. J. Med. Chem. 2011; 54: 2592
    CrossrefPubMed
  • 31 He Y, Yang J, Liu Q, Zhang X, Fan X. J. Org. Chem. 2020; 85: 15600
    CrossrefPubMed
  • 32 Wang M, Zhao J, Jiang X. ChemSusChem 2019; 12: 3064
    CrossrefPubMed
  • 33 Zhu H, Shen Y, Wen D, Le Z.-G, Tu T. Org. Lett. 2019; 21: 974
    CrossrefPubMed
  • 34 Wang M, Chen S, Jiang X. Org. Lett. 2017; 19: 4916
    CrossrefPubMed
    • 35a Muddala R, Acosta JA. M, Barbosa LC. A, Boukouvalas J. J. Nat. Prod. 2017; 80: 2166
      CrossrefPubMed
    • 35b Ehrich EW, Dallob A, Lepeleire ID, Hecken AV, Riendeau D, Yuan W, Porras A, Wittreich J, Seibold JR, Schepper PD, Mehlisch DR, Gertz B. Clin. Pharmacol. Ther. 1999; 65: 336
      CrossrefPubMed
  • 36 Evidente A, Sparapano L. J. Nat. Prod. 1994; 57: 1720
    CrossrefPubMed
  • 37 Zhou K, Zhang J, Qiu G, Wu J. Org. Lett. 2019; 21: 275
    CrossrefPubMed
  • 38 Fleming FF. Nat. Prod. Rep. 1999; 16: 597
    CrossrefPubMed
  • 39 López R, Palomo C. Angew. Chem. Int. Ed. 2015; 54: 13170
    CrossrefPubMed
  • 40 Dalpozzo R, Bartoli G, Bencivenni G. Chem. Soc. Rev. 2012; 41: 7247
    CrossrefPubMed
  • 41 Chen Z, Zhou Q, Wang Q.-L, Chen P, Xiong B, Liang Y, Tang K.-W, Liu Y. Adv. Synth. Catal. 2020; 362: 3004
    Crossref
  • 42 Zheng X, Zhong T, Yi X, Shen Q, Yin C, Zhang L, Zhou J, Chen J, Yu C. Adv. Synth. Catal. 2021; 363: 3359
    Crossref
  • 43 Gong X, Ding Y, Fan X, Wu J. Adv. Synth. Catal. 2017; 359: 2999
    CrossrefPubMed
  • 44 Yao Y, Yin Z, Chen W, Xie W, He F.-S, Wu J. Adv. Synth. Catal. 2021; 363: 570
    CrossrefPubMed
  • 45 Palmer JT, Rasnick D, Klaus JL, Brömme D. J. Med. Chem. 1995; 38: 3193
    CrossrefPubMed
  • 46 He F.-S, Yao Y, Xie W, Wu J. Adv. Synth. Catal. 2020; 362: 4744
    Crossref
  • 47 Huang J, Ding F, Chen Z, Yang G, Wu J. Org. Chem. Front. 2021; 8: 1461
    CrossrefPubMed
  • 48 The Chemistry of Functional Groups, Supplement S: The Chemistry­ of Sulphur-Containing Functional Groups . Patai S, Rappoport Z. Wiley; Chichester: 1993. doi.org/10.1002/recl.1995114080
    CrossrefGoogle Scholar
  • 49 Dang HT, Nguyen VT, Nguyen VD, Arman HT, Larionov OV. Org. Biomol. Chem. 2018; 16: 3605
    CrossrefPubMed
  • 50 Mukherjee P, Woroch CP, Cleary L, Rusznak M, Franzese RW, Reese MR, Tucker JW, Humphrey JM, Etuk SM, Kwan SC, am Ende CW, Ball ND. Org. Lett. 2018; 20: 3943
    CrossrefPubMed
  • 51 Zhong T, Pang M.-K, Chen Z.-D, Zhang B, Weng J, Lu G. Org. Lett. 2020; 22: 3072
    CrossrefPubMed
  • 52 Lan X.-W, Wang N.-X, Xing Y. Eur. J. Org. Chem. 2017; 5821
    CrossrefPubMed
  • 53 Kumar M, Ahmed R, Singh M, Sharma S, Thatikonda T, Singh PP. J. Org. Chem. 2020; 85: 716
    CrossrefPubMed
  • 54 Zhang J, An Y, Wu J. Chem. Eur. J. 2017; 23: 9477
    CrossrefPubMed
  • 55 Chen K, Chen W, Han B, Chen W, Liu M, Wu H. Org. Lett. 2020; 22: 1841
    CrossrefPubMed
  • 56 Baraldi PG, NuÇez MC, Morelli A, Falzoni S, Virgilio FD, Romagnoli R. J. Med. Chem. 2003; 46: 1318
    CrossrefPubMed
  • 57 You G, Xi D, Sun J, Hao L, Xia C. Org. Biomol. Chem. 2019; 17: 9479
    CrossrefPubMed
  • 58 Saavedra B, Marset X, Guillena G, Ramón DJ. Eur. J. Org. Chem. 2020; 3462
    Crossref
  • 59 Wang M, Fan Q, Jiang X. Green Chem. 2018; 20: 5469
    Crossref
  • 60 Wang Y, Du B, Sha W, Mei H, Han J, Pan Y. Org. Chem. Front. 2017; 4: 1313
    Crossref
  • 61 Li Y, Wang M, Jiang X. Chin. J. Chem. 2020; 38: 1521
    CrossrefPubMed
  • 62 Huang C.-M, Li J, Wang S.-Y, Ji S.-J. Chem. Lett. 2020; 31: 1923
    CrossrefPubMed
  • 63 Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527
    CrossrefPubMed
  • 64 Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
    CrossrefPubMed
  • 65 Speckmeier E, Fuchs PJ. W, Zeitler K. Chem. Sci. 2018; 9: 7096
    CrossrefPubMed
  • 66 Li H, Cheng Z, Tung C.-H, Xu Z. ACS Catal. 2018; 8: 8237
    CrossrefPubMed
  • 67 Yadav A, König K, Sharma AK, Singh KN. Org. Chem. Front. 2019; 6: 989
    CrossrefPubMed
  • 68 Gu L, Jin C, Wang W, He Y, Yang G, Li G. Chem. Commun. 2017; 53: 4203
    CrossrefPubMed
  • 69 Gong X, Yang M, Liu J.-B, He F.-S, Wu J. Org. Chem. Front. 2020; 7: 938
    CrossrefPubMed
  • 70 Weidne JP, Block SS. J. Med. Chem. 1964; 7: 671
    CrossrefPubMed
  • 71 Lv Y, Luo J, Ma Y, Dong Q, He L. Org. Chem. Front. 2021; 8: 2461
    CrossrefPubMed
  • 72 Gong X, Li X, Xie W, Wu J, Ye S. Org. Chem. Front. 2019; 6: 1863
    CrossrefPubMed
  • 73 He F.-S, Yao Y, Xie W, Wu J. Chem. Commun. 2020; 56: 9469
    CrossrefPubMed
  • 74 Liu N.-W, Liang S, Manolikakes G. Adv. Synth. Catal. 2017; 1308
    CrossrefPubMed
  • 75 Gong X, Wang M, Ye S, Wu J. Org. Lett. 2019; 21: 1156
    CrossrefPubMed
  • 76 Zhang J, Zhou K, Qiu G, Wu J. Org. Chem. Front. 2019; 6: 36
    CrossrefPubMed
  • 77 Gong X, Chen J, Lai L, Cheng J, Sun J, Wu J. Chem. Commun. 2018; 54: 11172
    CrossrefPubMed
  • 78 Zhang J, Li X, Xie W, Ye S, Wu J. Org. Lett. 2019; 21: 4950
    CrossrefPubMed
  • 79 Liu Y, Wang Q.-L, Chen Z, Li H, Xiong B.-Q, Zhang P.-L, Tang K.-W. Chem. Commun. 2020; 56: 3011
    CrossrefPubMed
  • 80 He F.-S, Ye S, Wu J. ACS Catal. 2019; 9: 8943
    CrossrefPubMed
  • 81 Wang X, Kuang Y, Ye S, Wu J. Chem. Commun. 2019; 55: 14962
    CrossrefPubMed
  • 82 Huang W, Cheng X. Synlett 2017; 28: 148
    CrossrefPubMed
  • 83 Gong X, Yang M, Liu J.-B, He F.-S, Fan X, Wu J. Green Chem. 2020; 22: 1906
    CrossrefPubMed
  • 84 Liu Y, Wang Q.-L, Chen Z, Chen P, Tang K.-W, Zhou Q, Xie J. Org. Biomol. Chem. 2019; 17: 10020
    CrossrefPubMed