Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with furan and thiophene: A novel method for hetero biaryl coupling

Tetrahedron

Volumn 58, Issue 40, 2002, Pages 8055-8058

  Demir, Ayhan S ^a   Reis, Ömer ^a   Emrullahoǧlu, Mustafa ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Arylcoupling; Furan; Manganese(III) acetate; Thiophene

Indexed keywords

ACETIC ACID DERIVATIVE; FURAN; MANGANESE ACETATE; MANGANESE DERIVATIVE; PHENYLHYDRAZINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOPHENE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; BIOAVAILABILITY; OXIDATION; PRIORITY JOURNAL; THIN LAYER CHROMATOGRAPHY;

EID: 0037201516     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01001-3     Document Type: Article

References (39)

1. Cooke R.G., Rae I.D. Aust. J. Chem. 17:1964;379.
2. Sorensen J.S., Sorensen N.A. Acta Chem. Scand. 12:1958;771.
3. Burkholder P.R., Pfister R.M., Leitz F.H. Appl. Microbiol. 14:1966;649.
4. (a) van Helden R., Verberg G. Recl. Trav. Chim. Pays-Bas. 84:1965;1263
5. (b) Norman R.O.C., Thomas C.B., Wilson J.S. J. Chem. Soc., Perkin Trans. 1. 1974;1289.
6. (a) Kozhevnikov I.V. React. Kinet. Catal. Lett. 5:1976;415
7. (b) Itahara T., Hashimoto M., Yumisashi H. Synthesis. 1984;255
8. (c) Eberson L., Gomez-Gonzales L. Acta Chem. Scand. 27:1973;1249.
9. Itahara T. J. Chem. Soc., Chem. Commun. 1980;49.
10. Itahara T. J. Org. Chem. 50:1985;5272.
11. Hashmi A.S.K., Ruppert T.L., Knöfel T., Bats J.W. J. Org. Chem. 62:1997;7295. and references cited therein.
12. (a) Williams P.L., Giralt E. Chem. Soc. Rev. 30:2001;145
13. (b) McClure S.M., Glover B., McSorley E., Millar A., Osterhout M.H., Roschangar F. Org. Lett. 3:2001;1677
14. (c) Brandao M.A.F., de Oliveira A.B., Snieckus V. Tetrahedron Lett. 34:1993;2437
15. (d) Takahashi K., Suzuki T., Akiyama K., Ikegami Y., Fukazawa Y. J. Am. Chem. Soc. 113:1991;4576.
16. (a) Gomberg M., Bachman W.E. J. Am. Chem. Soc. 46:1924;2339
17. (b) Johnson A.W. J. Am. Chem. Soc. 1946;895
18. (c) Beadle J.R., Korzeniowski S.H., Rosenberg D.E., Garcia-Slanga B.J., Gokel G.W. J. Org. Chem. 49:1984;1594.
19. Fisera L., Kovac J., Komanova E., Lesko J. Tetrahedron. 30:1974;4123.
20. Antonioletti R., D'Auria M., D'Onofrio F., Piancatelli G., Scettri A. J. Chem. Soc., Perkin Trans. 1. 1986;1755.
21. Fischer E. Justus Liebigs Ann. Chem. 190:1878;102.
22. Aylward J.B. J. Chem. Soc. B. 1969;1663.
23. Nakajima R., Kinosada M., Tamura T., Hara T. Bull. Chem. Soc. Jpn. 56:1983;1113.
24. Firouzabadi H., Mohajer D., Entezari-Moghodam M. Bull. Chem. Soc. Jpn. 61:1988;2185.
25. Barakat Z., Abdel-Wahad M.F., El-Sadr M.M. J. Chem. Soc. 1956;4685.
26. Demir A.S., Reis Ö., Özgül-Karaaslan E. J. Chem. Soc., Perkin Trans. 1. 2001;3042-3045.
27. Fleming I. Frontier Orbitals and Organic Chemical Reactions. 1998;Wiley-Interscience, New York. p 193.
28. (a) Tanis S.T., Deaton M.V., Dixon L.A., McWilliams M.C., Raggon J.W., Collins M.A. J. Org. Chem. 63:1998;6914
29. (b) Wolfe J.P., Singer R.A., Yang B.H., Buchwald S.L. J. Am. Chem. Soc. 121:1999;9550
30. (c) Mazza D.D., Reinecke M.G., Smith W.B. Magn. Reson. Chem. 27:1989;187
31. (d) Chadwick D.J., Chambers J., Meakins G.D., Snowden R.L. J. Chem. Soc., Perkin Trans. 1. 1973;201
32. (e) Hotta S., Kimura H., Lee S.A., Tamaki T. J. Heterocycl. Chem. 37:2000;281
33. (f) Kasemann R., Naumann D. J. Fluorine Chem. 48:1990;207
34. (g) Kamigata N., Yoshikawa M., Shimizu T. J. Fluorine Chem. 87:1998;91.
35. Varea T., Gonzales-Nunez M.E., Rodrigo-Chiner J., Asensio G. Tetrahedron Lett. 30:1989;4709.
36. (a) Demir A.S., Jeganathan A. Synthesis. 1992;235
37. (b) Demir A.S., Gerçek Z., Reis Ö., Duygu N., Arikan E. Tetrahedron. 55:1999;2441
38. (c) Demir A.S., Gerçek Z., Duygu N., Igdir A.C., Reis Ö. Can. J. Chem. 77:1999;1336
39. (d) Weinland R.F., Fischer G.Z. Anorg. Allg. Chem. 120:1992;161.