PDF herunterladen
Synthesis
DOI: 10.1055/a-2350-1248
paper
Recent Advancements in the Chemistry of Diazo Compounds

Visible-Light-Mediated gem-Difunctionalization of Diazo Compounds with Vinyl Sulfoxonium Ylides and Thiols

Srashti Bhardwaj
,
Raju Sen
,
Payel Adhikari
,
Janakiram Vaitla∗
This work was supported by the Science and Engineering Research Board (CRG/2023/000584).
› Weitere Informationen
    Lizenzen und Reprints Alle Artikel dieser Rubrik


Abstract

A visible-light-induced multicomponent reaction of vinyl sulfoxonium ylide, thiol, and diazo ester to generate tertiary sulfide is described. The present diastereoselective gem-difunctionalization of the diazo ester can be achieved under mild conditions, as it does not require any additives, catalysts, or transition metals and is tolerant of air and moisture. Due to more nucleophilicity, vinyl sulfoxonium ylide undergoes S–H insertion with thiols to generate an allyl sulfide intermediate. Simultaneously, diazo ester undergoes photolysis to generate a carbene intermediate. Subsequently, the coupling of carbene and allyl sulfide intermediates generates sulfonium ylide, which undergoes Doyle–Kirmse rearrangement to generate tertiary sulfide scaffolds.

Key words

visible light mediated reaction - metal-free transformation - carbenes - diazoacetates - sulfur ylides - sigmatropic rearrangement - stereoselective synthesis.

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2350-1248.
  • Supporting Information


Publikationsverlauf

Eingereicht: 08. Mai 2024

Angenommen nach Revision: 21. Juni 2024

Accepted Manuscript online:
21. Juni 2024

Artikel online veröffentlicht:
15. Juli 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Gillingham D, Fei N. Chem. Soc. Rev. 2013; 42: 4918
      CrossrefPubMed
    • 1b Ford A, Miel H, Ring A, Slattery CN, Maguire AR, McKervey MA. Chem. Rev. 2015; 115: 9981
      CrossrefPubMed
    • 1c Doyle MP, Duffy R, Ratnikov M, Zhou L. Chem. Rev. 2010; 110: 704
      CrossrefPubMed
    • 1d Soam P, Kamboj P, Tyagi V. Asian J. Org. Chem. 2021; 11: e202100570
      Crossref
    • 1e Davas DS, Bhardwaj S, Sen R, Gopalakrishnan DK, Vaitla J. Adv. Synth. Catal. 2022; 364: 3122
      Crossref
    • 2a Yang Z, Stivanin ML, Jurberg ID, Koenigs RM. Chem. Soc. Rev. 2020; 49: 6833
      CrossrefPubMed
    • 2b Durka J, Turkowska J, Gryko D. ACS Sustainable Chem. Eng. 2021; 9: 8895
      Crossref
    • 2c Ciszewski LW, Rybicka-Jasinska K, Gryko D. Org. Biomol. Chem. 2019; 17: 432
      CrossrefPubMed
    • 2d Empel C, Pei C, Koenigs RM. Chem. Commun. 2022; 58: 2788
      CrossrefPubMed
    • 2e Xuan J, Cai B. Chin.J. Org. Chem. 2021; 41: 4565
      Crossref
  • 3 Jurberg ID, Davies HM. L. Chem. Sci. 2018; 9: 5112
    CrossrefPubMed
    • 4a Bayer A, Vaitla J. Synthesis 2018; 51: 612
    • 4b Caiuby CA. D, Furniel LG, Burtoloso AC. B. Chem. Sci. 2022; 13: 1192
      CrossrefPubMed
    • 4c Cheng J, Wu X, Sun S, Yu J.-T. Synlett 2018; 30: 21
      Artikel in Thieme Connect
    • 4d Bisag GD, Ruggieri S, Fochi M, Bernardi L. Org. Biomol. Chem. 2020; 18: 8793
      CrossrefPubMed
    • 4e Sen R, Bhardwaj S, Bar K, Deshwal S, Vaitla J. Chem. Commun. 2023; 59: 12411
      CrossrefPubMed
    • 5a Trost BM. J. Am. Chem. Soc. 2002; 88: 1587
      Crossref
    • 5b Burtoloso AC. B, Dias RM. P, Leonarczyk IA. Eur. J. Org. Chem. 2013; 5005
      Crossref
    • 5c Zhang JJ, Schuster GB. J. Am. Chem. Soc. 2002; 111: 7149
      Crossref
    • 5d Xia XD, Lu LQ, Liu WQ, Chen DZ, Zheng YH, Wu LZ, Xiao WJ. Chem. Eur. J. 2016; 22: 8432
      CrossrefPubMed
    • 5e Pramanik MM. D, Yuan F, Yan DM, Xiao WJ, Chen JR. Org. Lett. 2020; 22: 2639
      CrossrefPubMed
    • 6a Li L, Deng K, Xing Y, Ma C, Ni SF, Wang Z, Huang Y. Nat. Commun. 2022; 13: 6588
      CrossrefPubMed
    • 6b Davas DS, Gopalakrishnan DK, Kumar S, Anmol, Karmakar T, Vaitla J. JACS Au 2024; 4: 1073
      CrossrefPubMed
  • 7 Echemendia R, de Oliveira KT, Burtoloso AC. B. Org. Lett. 2022; 24: 6386
    CrossrefPubMed
  • 8 Dong Y, Tian Y, Zhang Z, Wang T. Adv. Synth. Catal. 2022; 364: 4026
    Crossref
  • 9 Munaretto LS, Dos Santos CY, Gallo RD. C, Okada CY. Jr, Deflon VM, Jurberg ID. Org. Lett. 2021; 23: 9292
    CrossrefPubMed
  • 10 Ye C, Cai BG, Lu J, Cheng X, Li L, Pan ZW, Xuan J. J. Org. Chem. 2021; 86: 1012
    CrossrefPubMed
    • 11a Davas DS, Gopalakrishnan DK, Kumar D, Vaitla J. Org. Lett. 2022; 24: 8359
      CrossrefPubMed
    • 11b Bhardwaj S, Gopalakrishnan DK, Garg D, Vaitla J. JACS Au 2023; 3: 252
      CrossrefPubMed
    • 11c Davas DS, Gopalakrishnan DK, Bar K, Kumar S, Karmakar T, Vaitla J. Org. Lett. 2023; 25: 8992
      CrossrefPubMed
    • 11d Gopalakrishnan DK, Panigrahi S, Sen R, Vaitla J. Org. Lett. 2023; 25: 1519
      CrossrefPubMed
    • 11e Deshwal S, Davas DS, Bhardwaj S, Vaitla J. Org. Lett. 2024; 26: 809
      CrossrefPubMed
    • 12a Gopalakrishnan DK, Bhardwaj S, Kumar S, Karmakar T, Vaitla J. Chem. Commun. 2024; 60: 3846
      CrossrefPubMed
    • 12b Vaitla J, Bayer A, Hopmann KH. Angew. Chem. Int. Ed. 2018; 57: 16180
      CrossrefPubMed
  • 13 Bhardwaj S, Gopalakrishnan DK, Deshwal S, Sen R, Tiwari V, Karmakar T, Vaitla J. ACS Catal. 2024; 14: 2805
    Crossref
    • 14a Clayden J, Maclellan P. Beilstein J. Org. Chem. 2011; 7: 582
      CrossrefPubMed
    • 14b Yang XH, Davison RT, Dong VM. J. Am. Chem. Soc. 2018; 140: 10443
      CrossrefPubMed
  • 15 Qu C, Hao J, Ding H, Lv Y, Zhao XE, Zhao X, Wei W. J. Org. Chem. 2022; 87: 12921
    CrossrefPubMed
  • 16 Yang J, Wang J, Huang H, Qin G, Jiang Y, Xiao T. Org. Lett. 2019; 21: 2654
    CrossrefPubMed
  • 17 Hommelsheim R, Guo Y, Yang Z, Empel C, Koenigs RM. Angew. Chem. Int. Ed. 2019; 58: 1203
    CrossrefPubMed
  • 18 Orlowska K, Rybicka-Jasinska K, Krajewski P, Gryko D. Org. Lett. 2020; 22: 1018
    CrossrefPubMed
  • 19 Hu M, Ni C, Li L, Han Y, Hu J. J. Am. Chem. Soc. 2015; 137: 14496
    CrossrefPubMed