Synthesis 2013; 45(12): 1624-1626
DOI: 10.1055/s-0033-1338798
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Aerobic Oxidation of Propargyl Alcohol: A Convenient Method for the Synthesis of Propiolaldehyde

Jinxian Liu
a  Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China   Fax: +86(21)62609305   Email: [email protected]
b  College of Chemistry and Materials Science, Longyan University, Longyan 364012, P. R. of China
,
Shengming Ma*
a  Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China   Fax: +86(21)62609305   Email: [email protected]
c  State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 26 March 2013

Accepted after revision: 17 April 2013

Publication Date:
16 May 2013 (online)


Abstract

Propiolaldehyde was prepared by the oxidation of propargyl alcohol using molecular oxygen as the oxidant under atmospheric pressure and room temperature in a decent yield. Compared to the previous method with CrO3, such a protocol avoids the use of a stoichiometric amount of oxidant, and the workup procedure is much more eco-friendly and convenient affording a higher yield of the product.

Supporting Information

 
  • References

    • 1a Sauer JC. J. Am. Chem. Soc. 1957; 79: 5314
    • 1b Dabrowski J, Kamienska-Trela K. J. Am. Chem. Soc. 1976; 98: 2826
    • 1c Johnson F, Pillai KM. R, Grollman AP, Tseng L, Takeshita M. J. Med. Chem. 1984; 27: 954
    • 1d Gorgues A, Simon A, Le Coq A, Hercouet A, Corre F. Tetrahedron 1986; 42: 351
    • 1e Comasseto JV, Brandt CA. Synthesis 1987; 146
    • 1f Mo X.-S, Huang Y.-Z. Tetrahedron Lett. 1995; 36: 3539
    • 1g Berger D, Bartlome A, Neuenschwander M. Helv. Chim. Acta 1996; 79: 179
    • 2a Degl’Innocenti A, Capperucci A, Reginato G, Mordini A, Ricci A. Tetrahedron Lett. 1992; 33: 1507
    • 2b Seebach D, Beck AK, Schmidt B, Wang YM. Tetrahedron 1994; 50: 4363
    • 2c Sandanayaka VP, Feigelson GB, Prashad AS, Yang Y, Petersen PJ. Bioorg. Med. Chem. Lett. 2001; 11: 997
    • 2d Gusarova NK, Reutskaya AM, Ivanova NI, Medvedeva AS, Demina MM, Novopashin PS, Afonin AV, Albanov AI, Trofimov BA. J. Organomet. Chem. 2002; 67: 172
    • 2e Karama U, Höfle G. Eur. J. Org. Chem. 2003; 1042
    • 2f Xu D, Li Z, Ma S. Tetrahedron: Asymmetry 2003; 14: 3657
    • 3a Baldwin SW, Tomesch JC. J. Org. Chem. 1980; 45: 1455
    • 3b Matcheva K, Beckmann M, Schomburg D, Winterfeldt E. Synthesis 1989; 814
    • 3c Caprathe BW, Jaen JC, Wise LD, Heffner TG, Pugsley TA, Meltzer LT, Parvez M. J. Am. Chem. Soc. 1996; 118: 7513
    • 3d Guzmán A, Romero M, Talamás FX. J. Org. Chem. 1996; 61: 2470
    • 3e Bäurle S, Blume T, Mengel A, Parchmann C, Skuballa W, Bäsler S, Schäfer M, Sülzle D, Wrona-Metzinger H.-P. Angew. Chem. Int. Ed. 2003; 42: 3961
    • 3f Jones SB, Simmons B, Mastracchio A, MacMillan DW. C. Nature 2011; 475: 183
    • 4a Kobayashi K, Igura Y, Imachi S, Masui Y, Onaka M. Chem. Lett. 2007; 36: 60
    • 4b Jarowski PD, Wu Y.-L, Schweizer WB, Diederich F. Org. Lett. 2008; 10: 3347
    • 4c Creary X, Anderson A, Brophy C, Crowell F, Funk Z. J. Org. Chem. 2012; 77: 8756
  • 5 Li L, Zhang J. Org. Lett. 2011; 13: 5940
    • 6a Marnett LJ, Basu AK, O’Hara SM, Weller PE, Rahman AF. M. M, Oliver JP. J. Am. Chem. Soc. 1986; 108: 1348
    • 6b Caprathe BW, Jaen JC, Wise LD, Heffner TG, Pugsley TA, Meltzer LT, Parvez M. J. Med. Chem. 1991; 34: 2736
    • 6c Marcinek A, Adamus J, Huben K, Gebicki J, Bartczak TJ, Bednarek P, Bally T. J. Am. Chem. Soc. 2000; 122: 437
    • 6d Granum KA, Merkel G, Mulder JA, Debbins SA, Hsung RP. Tetrahedron 2012; 68: 9293
    • 7a Sauer JC. Org. Synth. 1956; 36: 66 ; Org. Synth. Coll. Vol. IV; Wiley: New York, 1963, 813
    • 7b Wille F, Saffer L, Weiskopf W. Justus Liebigs Ann. Chem. 1950; 568: 34
    • 7c Veliev MG, Guseinov MM. Synthesis 1980; 461
    • 7d van der Kerk SM, Boersma J, van der Kerk GJ. M. J. Organomet. Chem. 1981; 215: 303
    • 7e Kang YK, Lee KS, Yoo KH, Shin KJ, Kim DC, Lee C.-S, Kong JY, Kim DJ. Bioorg. Med. Chem. Lett. 2003; 13: 463
    • 7f Seburg RA, Hodges JA, McMahon RJ. Helv. Chim. Acta 2009; 92: 1626
  • 8 Lai TK, Banerji J, Chatterjee A, Basak B. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2005; 44: 1309
  • 9 Dubey A, Kandula SR. V, Kumar P. Synth. Commun. 2008; 38: 746
  • 10 Qian G, Zhao R, Lu G, Qi Y, Suo J. Synth. Commun. 2004; 34: 1753
  • 11 Ma S, Liu J, Li S, Chen B, Cheng J, Kuang J, Liu Y, Wan B, Wang Y, Ye J, Yu Q, Yuan W, Yu S. Adv. Synth. Catal. 2011; 353: 1005
  • 12 Liu J, Xie X, Ma S. Synthesis 2012; 44: 1569
  • 13 Szekelya J, Wang H, Peplowskia KM, Knutsona CG, Marnetta LJ, Rizzoa CJ. Nucleosides, Nucleotides Nucleic Acids 2008; 27: 103