Palladium/P(t-Bu)3-catalyzed synthesis of N-aryl azoles and application to the synthesis of 4,4',4''-tris(N-azolyl)triphenylamines

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 481-483

  Watanabe, Makoto ^a   Nishiyama, Masakazu ^a   Yamamoto, Toshihide ^a   Koie, Yasuyuki ^a  

^a TOSOH CORPORATION   (Japan)

Author keywords

Amination; Arylation; Azoles; Palladium catalysts; Phosphine

Indexed keywords

4,4',4'' TRIS(N AZOLYL)TRIPHENYLAMINE; ANILINE DERIVATIVE; BASE; CARBAZOLE DERIVATIVE; INDOLE; PALLADIUM; PHOSPHINE; PYRROLE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKALINITY; AMINATION; ARTICLE; CATALYST; LIGHT EMITTING DIODE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034700880     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02096-1     Document Type: Article

References (12)

1. (a) Kuwabara, Y.; Ogawa, H.; Inada, H.; Noma, N.; Shirota, Y. Adv. Mater. 1994, 6, 677-679.
2. (b) Hu, N.-X.; Xie, S.; Popovic, Z.; Ong, B.; Hor, A.-M. J. Am. Chem. Soc. 1999, 121, 5097-5098.
3. Maiorana, S.; Baldoli, C.; Buttero, P. D.; Ciolo, M. D.; Papagni, A. Synthesis 1998, 735-738 and references cited therein.
4. Arylation of imidazoles was recently reported, see: Kiyomori, A.; Marcoux, J.-F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657-2660.
5. Smith III, W. J.; Sawyer, J. S. Tetrahedron Lett. 1996, 37, 299-302.
6. Arylation of benzotriazole was reported, see: Beletskaya, I. P.; Davydov, D. V.; Moreno-Manas, M. Tetrahedron Lett. 1998, 39, 5617-5620.
7. Mann, G.; Hartwig, J. F.; Driver, M. S.; Rivas, C. F. J. Am. Chem. Soc. 1998, 120, 827-828.
8. 3 highly repressed debromination of aryl bromides in the reaction with piperazine, see: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620.
9. (b) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367-2370.
10. Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Speciality Chemicals 1998, 18, 445-450.
11. 3): δ=6.32 (d, J=2.0 Hz, 6H), 7.04 (d, J=2.0 Hz, 6H), 7.13 (d, J=6.1 Hz, 6H), 7.29 (d, J=6.1 Hz, 6H).
12. Compound 2 was isolated by reprecipitation from THF-MeOH. In Ref. 1a, 2 was prepared from triiodotriphenylamine with carbazole by the Ullmann protocol.