Palladium-catalyzed amination in the synthesis of polyazamacrocycles containing a 1,3-disubstituted benzene moiety

Synthesis

Volumn , Issue 19, 2007, Pages 2995-3012

  Averin, Alexei D ^a   Shukhaev, Anton V ^a   Golub, Svetlana L ^b   Buryak, Alexei K ^b   Beletskaya, Irina P ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b FRUMKIN INSTITUTE OF PHYSICAL CHEMISTRY AND ELECTROCHEMISTRY   (Russian Federation)

Author keywords

Aminations; Amines; Haloarenes; Homogenous catalysis; Macrocycles

Indexed keywords

AMINATIONS; HALOARENES; HOMOGENOUS CATALYSIS; MACROCYCLES;

BENZENE; CATALYSIS; DIMERS; PALLADIUM; SYNTHESIS (CHEMICAL);

AMINES;

2,5,8,11 TETRAAZABICYCLO[10.3.1]HEXADECA 1(16),12,14 TRIENE; 2,5,8,11,14 PENTAAZABICYCLO[13.3.1]NONADECA 1(19),15,17 TRIENE; 2,5,8,11,17,20,23,26 OCTAAZATRICYCLO[25.3.1.1 12,16]DOTRIACONTA 1(31),12,14,16(32),27,29 HEXAENE; 2,5,9,12 TETRAAZABICYCLO[11.3.1]HEPTADECA 1(17),13,15 TRIENE; 2,6,10 TRIAZABICYCLO[9.3.1]PENTADECA 1(15),11,13 TRIENE; 2,6,10,14 TETRAAZABICYCLO[13.3.1]NONADECA 1(19),15,17 TRIENE; 2,6,9,13 TETRAAZABICYCLO[12.3.1]OCTADECA 1(18),14,16 TRIENE; 5,8 DIOXA 2,11 DIAZABICYCLO[10.3.1]HEXADECA 1(16),12,14 TRIENE; 6,11 DIOXA 2,15 DIAZABICYCLO[14.3.1]EICOSA 1(20),16,18 TRIENE; BENZENE; MACROCYCLIC COMPOUND; PALLADIUM; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 35349003680     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990779     Document Type: Article

References (26)

1. Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Aza-Crown Macrocycles; Wiley & Sons: New York, 1993.
2. Burguette, M. I.; Escuder, B.; Garcia-Espana, E.; Luis, S. V.; Miravet, J. F. Tetrahedron 2002, 58, 2839.
3. Militsopoulou, M.; Tsiakopoulos, N.; Chochos, C.; Magoulas, G. Tetrahedron Lett. 2002, 43, 2593.
4. Favre-Reguillon, A.; Segat-Dioury, F.; Nait-Bouda, L.; Cosma, C.; Siaugue, J.-M.; Foos, J.; Guy, A. Synlett 2000, 868.
5. Ray, J. K.; Haldar, M. K.; Gupta, S.; Kar, G. K. Tetrahedron 2000, 56, 909.
6. De Wall, S. L.; Meadows, E. S.; Barbour, L. J.; Gokel, G. W. Chem. Commun. 1999, 1553.
7. Meadows, E. S.; De Wall, S. L.; Barbour, L. J.; Gokel, G. W. Chem. Commun. 1999, 1555.
8. Kubo, K.; Yamamoto, E.; Sakurai, T. Heterocycles 1998, 48, 2133.
9. Koulov, A. V.; Mahoney, J. M.; Smith, B. D. Org. Biomol. Chem. 2003, 1, 1467.
10. Vetrichelvan, M.; Lai, Y.-H.; Mok, K. F. Dalton Trans. 2003, 295.
11. Borisova, N. E.; Reshetova, M. D.; Ustynyuk, Yu. A. Chem. Rev. 2007, 107, 46.
12. Witulski, B.; Weber, M.; Bergsträsser, U.; Desvergne, J.-P.; Bassani, D. M.; Bouas-Laurent, H. Org. Lett. 2001, 3, 1467.
13. Gouloumis, A.; Lawson, R. G.; Vasquez, P.; Echegoyen, L.; Torres, T. Tetrahedron 2002, 58, 961.
14. Gunnlaugsson, T.; Nieuwenhuyzen, M.; Richard, L.; Thoss, V. J. Chem. Soc., Perkin Trans. 2 2002, 141.
15. (a) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
16. (b) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
17. Beletskaya, I. P.; Bessmertnykh, A. G.; Averin, A. D.; Denat, F.; Guilard, R. Eur. J. Org. Chem. 2005, 281.
18. Beletskaya, I. P.; Averin, A. D.; Pleshkova, N. A.; Borisenko, A. A.; Serebryakova, M. V.; Denat, F.; Guilard, R. Synlett 2005, 87.
19. Averin, A. D.; Ulanovskaya, O. A.; Borisenko, A. A.; Serebryakova, M. V.; Beletskaya, I. P. Tetrahedron Lett. 2006, 47, 2691.
20. Beletskaya, I. P.; Averin, A. D.; Ulanovskaya, O. A.; Fedotenko, I. A.; Borisenko, A. A.; Serebryakova, M. V.; Denat, F.; Guilard, R. Chem. Lett. 2005, 34, 1100.
21. Averin, A. D.; Ulanovskaya, O. A.; Fedotenko, I. A.; Borisenko, A. A.; Serebryakova, M. V.; Beletskaya, I. P. Helv. Chim. Acta 2005, 88, 1983.
22. Beletskaya, I. P.; Averin, A. D.; Borisenko, A. A.; Denat, F.; Guilard, R. Tetrahedron Lett. 2003, 44, 1433.
23. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144.
24. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
25. Beletskaya, I. P.; Bessmertnykh, A. G.; Averin, A. D.; Denat, F.; Guilard, R. Eur. J. Org. Chem. 2005, 261.
26. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.