Palladium-catalyzed direct arylation of thiazoles with aryl bromides

Tetrahedron

Volumn 59, Issue 30, 2003, Pages 5685-5689

  Yokooji, Aya ^a   Okazawa, Toru ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a   Nomura, Masakatsu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Aryl halides; Arylation; Palladium and compounds; Thiazoles

Indexed keywords

BROMINE DERIVATIVE; FLUORESCENT DYE; PALLADIUM; PHOSPHINE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0038306206     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00879-2     Document Type: Article

References (31)

1. (a) Dondoni A. Shinkai I. Comprehensive Heterocyclic Chemistry II. Vol. 3:1996;373 Pergamon, Glasgow, (b) Kalgutkar A.S., Crews B.C., Marnett L. J. Biochem. 35:1996;9076 (c) Hutchinson I., Stevens M.F.G., Westwell A.D. Tetrahedron Lett. 41:2000;425.
2. (a) Dondoni A. Shinkai I. Comprehensive Heterocyclic Chemistry II. Vol. 3:1996;373 Pergamon, Glasgow, (b) Kalgutkar A.S., Crews B.C., Marnett L. J. Biochem. 35:1996;9076 (c) Hutchinson I., Stevens M.F.G., Westwell A.D. Tetrahedron Lett. 41:2000;425.
3. (a) Dondoni A. Shinkai I. Comprehensive Heterocyclic Chemistry II. Vol. 3:1996;373 Pergamon, Glasgow, (b) Kalgutkar A.S., Crews B.C., Marnett L. J. Biochem. 35:1996;9076 (c) Hutchinson I., Stevens M.F.G., Westwell A.D. Tetrahedron Lett. 41:2000;425.
4. (a) Schwander H. Ullman's Encyclopedia of Industrial Chemistry. Vol. A11:1988;VCH, Weinheim. p 279 (b) Mori A., Sekiguchi A., Masui K., Shimada T., Horie M., Osakada K., Kawamoto M., Ikeda T. J. Am. Chem. Soc. 125:2003;1700 (c) Dölling K., Zaschke H., Schubert H. J. Prakt. Chem. 321:1979;643.
5. (a) Schwander H. Ullman's Encyclopedia of Industrial Chemistry. Vol. A11:1988;VCH, Weinheim. p 279 (b) Mori A., Sekiguchi A., Masui K., Shimada T., Horie M., Osakada K., Kawamoto M., Ikeda T. J. Am. Chem. Soc. 125:2003;1700 (c) Dölling K., Zaschke H., Schubert H. J. Prakt. Chem. 321:1979;643.
6. (a) Schwander H. Ullman's Encyclopedia of Industrial Chemistry. Vol. A11:1988;VCH, Weinheim. p 279 (b) Mori A., Sekiguchi A., Masui K., Shimada T., Horie M., Osakada K., Kawamoto M., Ikeda T. J. Am. Chem. Soc. 125:2003;1700 (c) Dölling K., Zaschke H., Schubert H. J. Prakt. Chem. 321:1979;643.
7. (a) Dietrich F., Stang P.J. Metal-catalyzed Cross-coupling Reactions. 1998;Wiley-VCH, Weinheim, (b) Miyaura N. Cross-Coupling Reactions. 2002;Springer, Berlin, (c) Li J.J., Gribble G.W. Palladium in Heterocyclic Chemistry. 2000;Pergamon, Amsterdam.
8. (a) Dietrich F., Stang P.J. Metal-catalyzed Cross-coupling Reactions. 1998;Wiley-VCH, Weinheim, (b) Miyaura N. Cross-Coupling Reactions. 2002;Springer, Berlin, (c) Li J.J., Gribble G.W. Palladium in Heterocyclic Chemistry. 2000;Pergamon, Amsterdam.
9. (a) Dietrich F., Stang P.J. Metal-catalyzed Cross-coupling Reactions. 1998;Wiley-VCH, Weinheim, (b) Miyaura N. Cross-Coupling Reactions. 2002;Springer, Berlin, (c) Li J.J., Gribble G.W. Palladium in Heterocyclic Chemistry. 2000;Pergamon, Amsterdam.
10. (a) Aoyagi Y., Inoue A., Koizumi I., Hashimoto R., Tokunaga K., Gohma K., Komatsu J., Sekine K., Miyafuji A., Kunoh J., Homma R., Akita Y., Ohta A. Heterocycles. 33:1992;257 (b) Miura M., Nomura M. Miyaura N. Cross-coupling Reactions. 2002;Springer, Berlin. p 211 (c) Hassan J., Sévignon M., Gozzi C., Schulz E., Lemaire M. Chem. Rev. 102:2002;1359.
11. (a) Aoyagi Y., Inoue A., Koizumi I., Hashimoto R., Tokunaga K., Gohma K., Komatsu J., Sekine K., Miyafuji A., Kunoh J., Homma R., Akita Y., Ohta A. Heterocycles. 33:1992;257 (b) Miura M., Nomura M. Miyaura N. Cross-coupling Reactions. 2002;Springer, Berlin. p 211 (c) Hassan J., Sévignon M., Gozzi C., Schulz E., Lemaire M. Chem. Rev. 102:2002;1359.
12. (a) Aoyagi Y., Inoue A., Koizumi I., Hashimoto R., Tokunaga K., Gohma K., Komatsu J., Sekine K., Miyafuji A., Kunoh J., Homma R., Akita Y., Ohta A. Heterocycles. 33:1992;257 (b) Miura M., Nomura M. Miyaura N. Cross-coupling Reactions. 2002;Springer, Berlin. p 211 (c) Hassan J., Sévignon M., Gozzi C., Schulz E., Lemaire M. Chem. Rev. 102:2002;1359.
13. (a) Pivsa-Art S., Satoh T., Kawamura Y., Miura M., Nomura M. Bull. Chem. Soc. Jpn. 71:1998;467 (b) Okazawa T., Satoh T., Miura M., Nomura M. J. Am. Chem. Soc. 124:2002;5286.
14. (a) Pivsa-Art S., Satoh T., Kawamura Y., Miura M., Nomura M. Bull. Chem. Soc. Jpn. 71:1998;467 (b) Okazawa T., Satoh T., Miura M., Nomura M. J. Am. Chem. Soc. 124:2002;5286.
15. Littke A.F., Fu G.C. Angew. Chem. Int. Ed. 41:2002;4176. and references therein.
16. (a) Goodson F.E., Wallow T.I., Novak B.M. J. Am. Chem. Soc. 119:1997;12441 (b) Grushin V.V. Organometallics. 19:2000;1888.
17. (a) Goodson F.E., Wallow T.I., Novak B.M. J. Am. Chem. Soc. 119:1997;12441 (b) Grushin V.V. Organometallics. 19:2000;1888.
18. Wolfe J.P., Buchwald S.L. Angew. Chem. Int. Ed. 38:1999;2413.
19. (a) A method for the selective 2-arylation of thiazole: Ref. 2b. Solvent effect on regioselectivity in the arylation of 3-furancarboxylate and 3-thiophenecarboxylate esters: (b) Glover B., Harvey K.A., Liu B., Sharp M.J., Tymoschenko M.F. Org. Lett. 5:2003;301. 2- or 4-Arylation of imidazole: (c) Sezen B., Sames D. J. Am. Chem. Soc. 125:2003;5274.
20. (a) A method for the selective 2-arylation of thiazole: Ref. 2b. Solvent effect on regioselectivity in the arylation of 3-furancarboxylate and 3-thiophenecarboxylate esters: (b) Glover B., Harvey K.A., Liu B., Sharp M.J., Tymoschenko M.F. Org. Lett. 5:2003;301. 2- or 4-Arylation of imidazole: (c) Sezen B., Sames D. J. Am. Chem. Soc. 125:2003;5274.
21. (a) A method for the selective 2-arylation of thiazole: Ref. 2b. Solvent effect on regioselectivity in the arylation of 3-furancarboxylate and 3-thiophenecarboxylate esters: (b) Glover B., Harvey K.A., Liu B., Sharp M.J., Tymoschenko M.F. Org. Lett. 5:2003;301. 2- or 4-Arylation of imidazole: (c) Sezen B., Sames D. J. Am. Chem. Soc. 125:2003;5274.
22. 5b.
23. Kametani Y., Satoh T., Miura M., Nomura M. Tetrahedron Lett. 41:2000;2655.
24. Begtrup M., Hansen L.B.L. Acta Chem. Scand. 46:1992;372.
25. Kashima C., Arao H. Synthesis. 1989;873.
26. Perry R.J. Chemtech. Feb. 1994;18.
27. Maeda M., Kojima M. J. Chem. Soc. Perkin Trans. 1. 1978;685.
28. Cohen V.I. J. Heterocycl. Chem. 16:1979;13.
29. Heinz J., Baumgärtel H. Chem. Ber. 103:1970;1572.
30. Kaltai E., Nyitrai J., Lempert K., Harváth G., Kalmán A., Argay G. Tetrahedron. 29:1973;2783.
31. Prager R.H., Smith J.A., Weber B., Williams C.M. J. Chem. Soc., Perkin Trans. 1. 1997;2665.