PDF herunterladen
Synthesis 2021; 53(17): 3037-3044
DOI: 10.1055/a-1467-2494
special topic
Bond Activation – in Honor of Prof. Shinji Murai

Late-Stage Derivatization of Buflavine by Nickel-Catalyzed Direct Substitution of a Methoxy Group via C–O Bond Activation

Ryoma Shimazumi
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
,
Kosuke Morita
b   Nada High School, Kobe, Hyogo 658-0082, Japan
,
Tomoki Yoshida
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
,
Kosuke Yasui
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
,
Mamoru Tobisu  ∗
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
c   Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan
› InstitutsangabenThis work was supported, in part, by the SEEDS program from Osaka University.
› Weitere Informationen
    Lizenzen und Reprints Alle Artikel dieser Rubrik


Dedicated to Professor Shinji Murai for his contribution to bond activation.

Abstract

The nickel-catalyzed cross-coupling of methoxyarenes was applied to buflavine, which allows for the selective monosubstitution of one of the two methoxy groups in the molecule, leading to the formation of 2- and 3-substituted isomers. Trimethylsilylmethyl (TMSCH2), phenyl, and alkynyl groups can be introduced into buflavine using this method. The resulting TMSCH2 analogue of buflavine can also be converted into several other derivatives.

Key words

C–O bond activation - cross-coupling - nickel - natural product - late-stage functionalization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1467-2494.
  • Supporting Information


Publikationsverlauf

Eingereicht: 10. März 2021

Angenommen nach Revision: 25. März 2021

Accepted Manuscript online:
25. März 2021

Artikel online veröffentlicht:
21. April 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Carlson EE. ACS Chem. Biol. 2010; 5: 639
    CrossrefPubMed
    • 2a White MC, Zhao J. J. Am. Chem. Soc. 2018; 140: 13988
      CrossrefPubMed
    • 2b Karimov RR, Hartwig JF. Angew. Chem. Int. Ed. 2018; 57: 4234
      CrossrefPubMed
    • 2c Cernak T, Dykstra KD, Tyagarajan S, Vachal P, Krska SW. Chem. Soc. Rev. 2016; 45: 546
      CrossrefPubMed
    • 3a Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
      CrossrefPubMed
    • 3b Tobisu M, Chatani N. Top. Organomet. Chem. 2013; 44: 35
      CrossrefPubMed
    • 3c Tobisu M, Chatani N. Nickel-Catalyzed Cross-Coupling Reactions of Unreactive Phenolic Electrophiles via C–O Bond Activation. In Ni- and Fe-Based Cross-Coupling Reactions . Correa A. Springer; Cham: 2017: 129-156
      CrossrefGoogle Scholar
    • 3d Tobisu M, Chatani N. Metal-Catalyzed Aromatic C–O Bond Activation/Transformation. In Organometallics for Green Catalysis. Topics in Organometallic Chemistry, Vol. 63. Dixneuf PH, Soulé J.-F. Springer; Cham: 2018: 103-140
      CrossrefGoogle Scholar
    • 3e Tobisu M. C–O Bond Transformations. In Nickel Catalysis in Organic Synthesis: Methods and Reactions . Ogoshi S. Wiley-VCH; Weinheim: 2020: 123-150
      Google Scholar

      • Reviews from other groups:
    • 3f Li B.-J, Yu D.-G, Sun C.-L, Shi Z.-J. Chem. Eur. J. 2011; 17: 1728
      CrossrefPubMed
    • 3g Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A.-M, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346
      CrossrefPubMed
    • 3h Yamaguchi J, Muto K, Itami K. Eur. J. Org. Chem. 2013; 19
    • 3i Cornella J, Zarate C, Martin R. Chem. Soc. Rev. 2014; 43: 8081
      CrossrefPubMed
    • 3j Qiu Z, Li C.-J. Chem. Rev. 2020; 120: 10454
      CrossrefPubMed
    • 4a Tobisu M, Takahira T, Chatani N. Org. Lett. 2015; 17: 4352
      CrossrefPubMed
    • 4b Tobisu M, Takahira T, Ohtsuki A, Chatani N. Org. Lett. 2015; 17: 680
      CrossrefPubMed
    • 4c Tobisu M, Yasutome A, Kinuta H, Nakamura K, Chatani N. Org. Lett. 2014; 16: 5572
      CrossrefPubMed
    • 4d Morioka T, Nishizawa A, Nakamura K, Tobisu M, Chatani N. Chem. Lett. 2015; 44: 1729
      Crossref
    • 4e Tobisu M, Takahira T, Morioka T, Chatani N. J. Am. Chem. Soc. 2016; 138: 6711
      CrossrefPubMed
    • 4f Igarashi T, Haito A, Chatani N, Tobisu M. ACS Catal. 2018; 8: 7475
      Crossref
    • 5a Álvarez-Bercedo P, Martin R. J. Am. Chem. Soc. 2010; 132: 17352
      CrossrefPubMed
    • 5b Wang C, Ozaki T, Takita R, Uchiyama M. Chem. Eur. J. 2012; 18: 3482
      CrossrefPubMed
    • 5c Leiendecker M, Hsiao C.-C, Guo L, Alandini N, Rueping M. Angew. Chem. Int. Ed. 2014; 53: 12912
      CrossrefPubMed
    • 5d Wang T.-H, Ambre R, Wang Q, Lee W.-C, Wang P.-C, Liu Y, Zhao L, Ong T.-G. ACS Catal. 2018; 8: 11368
      Crossref
  • 6 Isolation of 1: Viladomat F, Bastida J, Codina C, Campbell WE, Mathee S. Phytochemistry 1995; 40: 307
    CrossrefPubMed

      • Biological activity of 1:
    • 7a Ishida Y, Sasaki Y, Kimura Y, Watanabe K. J. Pharmacobio-Dyn. 1985; 8: 917
      CrossrefPubMed
    • 7b Ishida Y, Watanabe K, Kobayashi S, Kihara M. Chem. Pharm. Bull. 1977; 25: 1851
      CrossrefPubMed

      Unique reactivity of IMesMe in nickel-catalyzed inert bond activation:
    • 8a Tobisu M, Yasui K, Aihara Y, Chatani N. Angew. Chem. Int. Ed. 2017; 56: 1877
      CrossrefPubMed
    • 8b Morioka T, Nishizawa A, Furukawa T, Tobisu M, Chatani N. J. Am. Chem. Soc. 2017; 139: 1416
      CrossrefPubMed
    • 8c Yasui K, Chatani N, Tobisu M. Org. Lett. 2018; 20: 2108
      CrossrefPubMed
    • 8d See also ref. 4f
    • 9a Das M, O’Shea DF. Tetrahedron 2013; 69: 6448
      Crossref
    • 9b Zhang W.-X, Ding C.-H, Luo Z.-B, Hou X.-L, Dai L.-X. Tetrahedron Lett. 2006; 47: 8391
      Crossref
    • 10a Barreiro EJ, Kümmerle AE, Fraga CA. M. Chem. Rev. 2011; 111: 5215
      CrossrefPubMed
    • 10b Schönherr H, Cernak T. Angew. Chem. Int. Ed. 2013; 52: 12256
      CrossrefPubMed
  • 11 Kinuta H, Tobisu M, Chatani N. J. Am. Chem. Soc. 2015; 137: 1593
    CrossrefPubMed
  • 12 Kosama S, Takita H, Kajimoto T, Nishide K, Node M. Tetrahedron 2004; 60: 4901
    Crossref
  • 13 Dong Z, Wang J, Dong G. J. Am. Chem. Soc. 2015; 137: 5887
    CrossrefPubMed
  • 14 Wertz S, Leifert D, Studer A. Org. Lett. 2013; 15: 928
    CrossrefPubMed
  • 15 Bariwal JB, Ermolat’ev DS, Glasnov TN, Hecke KV, Mehta VP, Meervelt LV, Kappe CO, Van der Eycken EV. E. Org. Lett. 2010; 12: 2774
    CrossrefPubMed
  • 16 Jian Y, Sun G, Li J, Su D, Li C, Zhong G. Chin. J. Chem. 2011; 29: 1423
    Crossref