Download PDF
Synlett 2022; 33(08): 800-804
DOI: 10.1055/a-1799-7464
letter

Acetalization of Enol Ethers with Alcohols under Visible Light Irradiation Using BINOLs as Photoacid Catalysts

Haonan Liu
a   Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350116, P. R. of China
,
Yueyong Chen
a   Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350116, P. R. of China
,
Deng An
a   Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350116, P. R. of China
,
Xun Zhang∗
a   Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350116, P. R. of China
,
Saihu Liao  ∗
a   Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350116, P. R. of China
b   Beijing National Laboratory for Molecular Sciences (BNLMS), Beijing 100190, P. R. of China
› Author AffiliationsWe gratefully acknowledge the Recruitment Program of Global Experts, the Beijing National Laboratory for Molecular Sciences (BNLMS201913), and Fuzhou University for the financial support.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

Appropriately substituted 1,1′-bi-2-naphthols (BINOLs) are demonstrated as effective photoacid catalysts for promoting the acetalization of enol ethers with alcohols under irradiation with visible light. The reactions proceed efficiently with a wide range of substrates under mild, near neutral conditions.

Key words

BINOL - photoacids - acetals - visible light - acetalization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1799-7464.
  • Supporting Information


Publication History

Received: 17 January 2022

Accepted after revision: 15 March 2022

Accepted Manuscript online:
15 March 2022

Article published online:
19 April 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Yu M, Pagenkopf BL. Tetrahedron 2003; 59: 2765
      Crossref
    • 1b Čorić I, List B. Nature 2012; 483: 315
      CrossrefPubMed
    • 1c Kim JH, Čorić I, Palumbo C, List B. J. Am. Chem. Soc. 2015; 137: 1778
      CrossrefPubMed
    • 2a Kotke M, Schreiner PR. Tetrahedron 2006; 62: 434
      Crossref
    • 2b Showler AJ, Darley PA. Chem. Rev. 1967; 67: 427
      CrossrefPubMed
    • 3a Prier CK, Rankic DA, MacMillan DW. Chem. Rev. 2013; 113: 5322
      CrossrefPubMed
    • 3b Schultz DM, Yoon TP. Science 2014; 343: 985
      CrossrefPubMed
    • 3c Chen J.-R, Yan D.-M, Wei Q, Xiao W.-J. ChemPhotoChem 2017; 1: 148
      Crossref
    • 3d Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
      CrossrefPubMed
    • 3e Ravelli D, Protti S, Fagnoni M. Chem. Rev. 2016; 116: 9850
      CrossrefPubMed
    • 3f Oates RP, Jones PB. J. Org. Chem. 2008; 73: 4743
      CrossrefPubMed
  • 4 Yi H, Niu L, Wang S, Liu T, Lei A. Org. Lett. 2017; 19: 122
    CrossrefPubMed
  • 5 Zhao G, Wang T. Angew. Chem. Int. Ed. 2018; 130: 6228
    Crossref
    • 6a Chen Y, Yekta S, Yudin AK. Chem. Rev. 2003; 103: 3155
      CrossrefPubMed
    • 6b Akiyama T. Chem. Rev. 2007; 107: 5744
      CrossrefPubMed
    • 6c Asymmetric Organocatalysis. Topics in Current Chemistry; List B. In Berlin/Heidelberg: Springer-Verlag; 2009 Vol. 291..
      PubMedGoogle Scholar
    • 7a Das A, Ayad S, Hanson K. Org. Lett. 2016; 18: 5416
      CrossrefPubMed
    • 7b Wan P, Shukla D. Chem. Rev. 1993; 93: 571
      Crossref
    • 7c Tolbert LM, Haubrich JE. J. Am. Chem. Soc. 1990; 112: 8163
      Crossref
    • 7d Tolbert LM, Solntsev KM. Acc. Chem. Res. 2002; 35: 19
      CrossrefPubMed
    • 7e Shi Z, Peng P, Strohecker D, Liao Y. J. Am. Chem. Soc. 2011; 133: 14699
      CrossrefPubMed
    • 7f Iwata R, Uda K, Takahashi D, Toshima K. Chem. Commun. 2014; 50: 10695
      CrossrefPubMed
  • 8 Nishikubo Y, Kanzaki S, Matsumura S, Toshima K. Tetrahedron Lett. 2006; 47: 8125
    Crossref
    • 9a Peretz-Soroka H, Pevzner A, Davidi G, Naddaka V, Kwiat M, Huppert D, Patolsky F. Nano Lett. 2015; 15: 4758
      CrossrefPubMed
    • 9b Peretz-Soroka H, Pevzner A, Davidi G, Naddaka V, Tirosh R, Flaxer E, Patolsky F. Nano Lett. 2013; 13: 3157
      CrossrefPubMed
  • 10 Das A, Banerjee T, Hanson K. Chem. Commun. 2016; 52: 1350
    CrossrefPubMed
  • 11 Ma Q, Zhang X, Ji L, Liao S. Polym. Chem. 2019; 10: 6662
    Crossref
    • 12a Fan XZ, Rong JW, Wu HL, Zhou Q, Deng HP, Tan JD, Xue CW, Wu LZ, Tao HR, Wu J. Angew. Chem. Int. Ed. 2018; 57: 8514
      CrossrefPubMed
    • 12b Zhou QQ, Zou YQ, Lu LQ, Xiao WJ. Angew. Chem. Int. Ed. 2019; 58: 1586
      CrossrefPubMed
  • 13 Ni X, Li X, Li Z, Cheng JP. Org. Chem. Front. 2016; 3: 1154
    Crossref
  • 14 Wilger DJ, Grandjean JM, Lammert TR, Nicewicz DA. Nat. Chem. 2014; 6: 720
    CrossrefPubMed