On the oxidative coupling of N,N-disubstituted 2-aminothiophenes - Synthesis of N,N′-persubstituted 5,5′-diamino-2,2′- bithiophenes

Tetrahedron

Volumn 60, Issue 37, 2004, Pages 8213-8219

  Zeika, Olaf ^a   Hartmann, Horst ^b  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF APPLIED SCIENCES   (Germany)

Author keywords

2 Aminothiophenes; 5,5 Diamino 2,2 bithiophenes; 5,5 Dihydro 2,2 bithiophene 5,5 diiminium salts; Hetaryl hetaryl coupling; Oxidative coupling

Indexed keywords

OXIDIZING AGENT; THIOPHENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; ELECTRONICS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 4143118016     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.107     Document Type: Article

References (27)

1. M.S. Gibson S. Patai The Chemistry of the Amino Group 1968 Wiley New York 37 77
2. G. Spielberger, H. Glaser, F. Möller, and R. Schröter E. Müller Houben-Weyl, Methoden der Organischen Chemie Vol. 11/1 1957 Georg Thieme Stuttgart 24 267
3. A.W. Thomas, and S.V. Levy Angew. Chem., Int. Ed. Engl. 42 2003 5400 5449 and references given therein
4. J.F. Hartwig Angew. Chem. 110 1998 2154 2177
5. J.F. Hartwig Angew. Chem., Int. Ed. Engl. 37 1998 2046
6. J. Louie, and J.F. Hartwig Tetrahedron 36 1995 3609 3612
7. A.S. Guram, R.A. Rennels, and S.L. Buchwald Angew. Chem., Int. Ed. Engl. 34 1995 1348 1350
8. D. Prim, J.-M. Campagne, D. Joseph, and B. Andrioletti Tetrahedron 2041 2002 2075
9. E. Lukevics, P. Arsenyan, and O. Pudova Heterocycles 60 2003 663 687
10. J.F. Hartwig E. Negishi Palladium-catalysed amination of aryl hablides and related reactions Handbook of Organopalladium Chemistry for Organic Synthesis 2002 Wiley New York 1051 1096
11. M. Watanabe, T. Yamamoto, and M. Nishiyama Chem. Commun. 2000 133
12. K.-T. Wong, T.H. Hung, S.C. Kao, C.H. Chou, and Y.O. Su Chem. Commun. 2001 1628 1629
13. P. Gerstner, D. Rohde, and H. Hartmann Synthesis 2002 2487 2489
14. P.V. Bedworth, Y. Cai, A. Jen, and S.R. Marder J. Org. Chem. 61 1996 2242 2246
15. C.R. Moylan, R.J. Twieg, V.Y. Lee, R.D. Miller, W. Volksen, J.I. Thackara, and C.A. Walsh SPIE 2285 1994 17 30
16. I.-Y. Wu, J.T. Lin, Y.-T. Tao, E. Balasabramaniam, Y.Y. Su, and C.-W. Ko Chem. Mater. 13 2001 2626 2631
17. Y.Z. Su, J.T. Lin, Y.-T. Tao, C.-W. Ko, S.-C. Lin, and S.-S. Sun Chem. Mater. 14 2002 1884 1890
18. (a) I.-Y. Wu, J.T. Lin, Y.-T. Tao, and E. Balasabramaniam Adv. Mater. 12 2000 668 669
19. (b) E. Ueta, H. Nakeno, and Y. Shirota Chem. Lett. 1994 2397 2398
20. Shoshi, M.; Shizuoka, N.; Sasaki, M.; Shizuoka, S. DE 3439113 (1984); Chem. Abstr. 1986, 104, 59361.
21. O. Zeika, and H. Hartmann Synthesis 2004 377 380
22. J. Schumann, A. Kanitz, and H. Hartmann Synthesis 2002 1268 1276
23. H. Hartmann, P. Gerstner, and D. Rohde Org. Lett. 3 2001 1673 1675
24. E.T. Seo, R.F. Nelson, J.M. Fritsch, L.S. Marcoux, D.W. Leddy, and R.N. Adams J. Am. Chem. Soc. 88 1966 3498 3503
25. S.C. Creason, J. Wheeler, and R.F. Nelson J. Org. Chem. 37 1972 4440 4446
26. O. Hamerich, and V.D. Parker Adv. Phys. Org. Chem. 20 1984 55 189
27. H. Tohma, M. Iwata, T. Maegawa, Y. Kiyono, A. Maruyama, and Y. Kita Org. Biomol. Chem. 2003 1647 1649