Aerobic oxidation of propargyl alcohol: A convenient method for the synthesis of propiolaldehyde

Synthesis (Germany)

Volumn 45, Issue 12, 2013, Pages 1624-1626

  Liu, Jinxian ^a,b   Ma, Shengming ^a,c  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b LONGYAN UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

aerobic oxidation; iron nitrate; propargyl alcohol; sodium chloride; TEMPO

Indexed keywords

AEROBIC OXIDATIONS; ECO-FRIENDLY; HIGHER YIELD; IRON NITRATES; PROPARGYL ALCOHOL; ROOM TEMPERATURE; TEMPO;

ATMOSPHERIC PRESSURE; OXIDANTS; SODIUM CHLORIDE;

OXIDATION;

ALCOHOL; ALDEHYDE; CHROMIUM; OXYGEN; PROPARGYL ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DIELS ALDER REACTION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STOICHIOMETRY; SYNTHESIS;

EID: 84878776927     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1338798     Document Type: Article

References (32)

1. Sauer J. C. J. Am. Chem. Soc.: 1957; 79 5314
2. Dabrowski J., Kamienska-Trela K. J. Am. Chem. Soc.: 1976; 98 2826
3. Johnson F., Pillai K. M. R, Grollman A. P., Tseng L., Takeshita M. J. Med. Chem.: 1984; 27 954
4. Gorgues A., Simon A., Le Coq A., Hercouet A., Corre F. Tetrahedron: 1986; 42 351
5. Comasseto J. V., Brandt C. A. Synthesis: 1987; 146
6. Mo X.-S, Huang Y.-Z. Tetrahedron Lett.: 1995; 36 3539
7. Berger D., Bartlome A., Neuenschwander M. Helv. Chim. Acta: 1996; 79 179
8. Degl'Innocenti A., Capperucci A., Reginato G., Mordini A., Ricci A. Tetrahedron Lett.: 1992; 33 1507
9. Seebach D., Beck A. K., Schmidt B., Wang Y. M. Tetrahedron: 1994; 50 4363
10. Sandanayaka V. P., Feigelson G. B., Prashad A. S., Yang Y., Petersen P. J. Bioorg. Med. Chem. Lett.: 2001; 11 997
11. Gusarova N. K., Reutskaya A. M., Ivanova N. I., Medvedeva A. S., Demina M. M., Novopashin P. S., Afonin A. V., Albanov A. I., Tromov B. A. J. Organomet. Chem.: 2002; 67 172
12. Karama U., Höfle G. Eur. J. Org. Chem.: 2003; 1042
13. Xu D., Li Z., Ma S. Tetrahedron: Asymmetry: 2003; 14 3657
14. Baldwin S. W., Tomesch J. C. J. Org. Chem.: 1980; 45 1455
15. Matcheva K., Beckmann M., Schomburg D., Winterfeldt E. Synthesis: 1989; 814
16. Caprathe B. W., Jaen J. C., Wise L. D., Heffner T. G., Pugsley T. A., Meltzer L. T., Parvez M. J. Am. Chem. Soc.: 1996; 118 7513
17. Guzmán A., Romero M., Talamás F. X. J. Org. Chem.: 1996; 61 2470
18. 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
19. Jones S. B., Simmons B., Mastracchio A., MacMillan D. W. C. Nature: 2011; 475 183
20. Kobayashi K., Igura Y., Imachi S., Masui Y., Onaka M. Chem. Lett.: 2007; 36 60
21. Jarowski P. D., Wu Y.-L, Schweizer W. B., Diederich F. Org. Lett.: 2008; 10 3347
22. Creary X., Anderson A., Brophy C., Crowell F., Funk Z. J. Org. Chem.: 2012; 77 8756
23. Marnett L. J., Basu A. K., O'Hara S. M., Weller P. E., Rahman A. F. M. M, Oliver J. P. J. Am. Chem. Soc.: 1986; 108 1348
24. Caprathe B. W., Jaen J. C., Wise L. D., Heffner T. G., Pugsley T. A., Meltzer L. T., Parvez M. J. Med. Chem.: 1991; 34 2736
25. Marcinek A., Adamus J., Huben K., Gebicki J., Bartczak T. J., Bednarek P., Bally T. J. Am. Chem. Soc.: 2000; 122 437
26. Granum K. A., Merkel G., Mulder J. A., Debbins S. A., Hsung R. P. Tetrahedron: 2012; 68 9293
27. Sauer J. C. Org. Synth.: 1956; 36 66; Org. Synth. Coll. Vol. IV; Wiley: New York, 1963, 813
28. Wille F., Saffer L., Weiskopf W. Justus Liebigs Ann. Chem.: 1950; 568 34
29. Veliev M. G., Guseinov M. M. Synthesis: 1980; 461
30. van der Kerk S. M., Boersma J., van der Kerk G. J. M. J. Organomet. Chem.: 1981; 215 303
31. Kang Y. K., Lee K. S., Yoo K. H., Shin K. J., Kim D. C., Lee C.-S, Kong J. Y., Kim D. J. Bioorg. Med. Chem. Lett.: 2003; 13 463
32. Seburg R. A., Hodges J. A., McMahon R. J. Helv. Chim. Acta: 2009; 92 1626