Skip to main content
SpringerLink
Log in

Sonogashira coupling reaction of homopropargyl ether with aryl bromides and synthesis of 2,5-disubstituted 3-bromofurans

  • Published:
Science in China Series B: Chemistry Aims and scope Submit manuscript

Abstract

This paper presents Sonogashira coupling reaction of aryl bromides with protected homopropargyl alcohols such as tert-butyldimethyl(1-phenylbut-3-ynyloxy)silane and tert-butyldimethyl(1-(2,4-dichlorophenyl)but-3-ynyloxy)silane in piperidine catalyzed by PdCl2/PPh3 without copper(I). The coupling products, disubstituted acetylene, are obtained in good or excellent yields. These products can be further used for the synthesis of 2,5-disubstituted 3-bromofurans.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Organ M G., Ghasemi H. Metal-catalyzed coupling reactions on an olefin template: The total synthesis of (13E,15E,18Z,20Z)-1-hy-droxypentacosa-13,15,18,20-tetraen-11-yn-4-one-1-acetate. J Org Chem, 2004, 69: 695–700

    Article  CAS  Google Scholar 

  2. Ohyabu N, Nishikawa T, Isobe M. First asymmetric total synthesis of tetrodotoxin. J Am Chem Soc, 2003, 125: 8798–8805

    Article  CAS  Google Scholar 

  3. Altenburger J M, Lassalle G. Y, Matrougui M, Galtier D, Jetha J C, Bocskei Z, Berry C N, Lunven C, Lorrain J, Herault J P, Schaeffer P, O’Connor S E, Herbert J M. SSR182289A, a selective and potent orally active thrombin inhibitor. Bioorg Med Chem, 2004, 12: 1713–1730

    Article  CAS  Google Scholar 

  4. Dai W M, Lai K W, Wu A, Hamaguchi W, Lee M Y H, Zhou L, Ishii A, Nishimoto S. DNA cleavage potency, cytotoxicity, and mechanism of action of a novel class of enediyne prodrugs. J Med Chem, 2002, 45: 758–761

    Article  CAS  Google Scholar 

  5. Lee S H, Nakamura T, Tsutsui T. Synthesis and characterization of oligo(9,9-dihexyl-2,7-fluorene ethynylene)s: For application as blue light-emitting diobe. Org Lett, 2001, 3: 2005–2007

    Article  CAS  Google Scholar 

  6. Sonogashira K, Tohda Y, Hagihara N. A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett, 1975, 16: 4467–4470

    Article  Google Scholar 

  7. Dieck H, Heck F R. Palladium catalyzed synthesis of aryl, heterocyclic and vinylic acetylene derivatives. J Organomet Chem, 1975, 93: 259–263

    Article  CAS  Google Scholar 

  8. Rafael C, Carmen Na’jera. The Sonogashira reaction: A booming methodology in synthetic organic chemistry. Chem Rev, 2007, 107: 874–922

    Article  CAS  Google Scholar 

  9. Lee A S Y, Chu S F, Chang Y T, Wang S H. Synthesis of homopropargyl alcohols via sonochemical Barbier-type reaction. Tetrahedron Lett, 2004, 45: 1551–1553

    Article  CAS  Google Scholar 

  10. Masuyama Y, Ito A, Fukuzawa M, Terada K, Kurusu Y. Carbonyl propargylation or allenylation by 3-haloprop-1-yne with tin(II) halides and tetrabutylammonium halides. Chem Commun, 1998, 2025–2026

  11. Li Q R, Gu C Z, Yin H. Tin-Indium mediated and microwave assisted propargylation of aldehydes with propargyl bromide. Chin J Chem, 2006, 1: 72–78

    Article  Google Scholar 

  12. Kundu A, Prabhakar S, Vairamani M, Roy S. A novel copper(II)/tin(II) reagent for regio- and chemoselective carbonyl propargylation. Organometallics, 1999, 18: 2782–2785

    Article  CAS  Google Scholar 

  13. Adam S, Kraig A W, Roman D. 5-Endo-dig electrophilic cyclization of 1,4-disubstituted but-3-yn-1-ones: regiocontrolled synthesis of 2,5-disubstituted 3-bromo- and 3-iodofurans. Org Lett, 2005, 7: 1769–1772

    Article  CAS  Google Scholar 

  14. Chini M, Crotti P, Favero L, Macchia F. Stereo- and regioselective metal salt-catalyzed alkynylation of 1,2-epoxides. Tetrahedron Lett, 1991, 32: 6617–6620

    Article  CAS  Google Scholar 

  15. Padwa A, Crumrine D S, Hartman R B, Layton R. Photochemical cyclobutanol formation of an aryl ketone scope and mechanism of the reaction. J Am Chem Soc, 1967, 89: 4435–4442

    Article  CAS  Google Scholar 

  16. Burns M R, Coward J K. A facile one-pot synthesis of homopropargylic alcohols from terminal acetylenes. J Org Chem, 1993, 58: 528–532

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. State Key Laboratory and Research Institute of Elemento-organic Chemistry, Nankai University, Tianjin, 300071, China

    Xin Wang, LingYan Liu, WeiXing Chang & Jing Li

Authors
  1. Xin Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. LingYan Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. WeiXing Chang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jing Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jing Li.

Additional information

Supported by the National Natural Science Foundation of China (Grant No. 20421202 & 20372033)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, X., Liu, L., Chang, W. et al. Sonogashira coupling reaction of homopropargyl ether with aryl bromides and synthesis of 2,5-disubstituted 3-bromofurans. Sci. China Ser. B-Chem. 52, 1314–1320 (2009). https://doi.org/10.1007/s11426-009-0203-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-009-0203-z

Keywords

Search

Navigation