Abstract
Palladium-catalyzed C-N-cross-coupling of N,N′-bis(bromobenzyl) diazacrown compounds with two equivalents of 1-aza-15-crown-5 and 1-aza-18-crown-6 ethers furnished trismacrocyclic compounds with isolated macrocycles. Macrotricyclic cryptands were obtained when diazacrown ethers were used as N-components.
Similar content being viewed by others
References
A. M. Costero, S. Gil, J. Sanchis, S. Peransi, V. Sanzam, J. A. G. Williams, Tetrahedron, 2004, 60, 6327.
H. Schmittel, J. Chem. Soc., Chem. Commun., 1995, 687.
P. D. Beer, A. D. Keefe, H. Sikanyika, C. Blackburn, J. F. McAleer, J. Chem. Soc., Dalton Trans., 1990, 3289.
L. Michaudet, P. Richard, B. Boitrel, Tetrahedron Lett., 2000, 41, 8289.
H. Chen, Y. S. Kim, J. Lee, S. J. Yoon, D. S. Lim, H.-J. Choi, K. Koh, Sensors, 2007, 7, 2263.
R. C. Helgeson, T. L. Tarnowski, J. M. Timko, D. J. Cram, J. Am. Chem. Soc., 1977, 99, 6411.
O. E. Sielcken, M. M. van Tilborg, M. F. M. Roks, R. Hendriks, W. Drenth, R. J. M. Nolte, J. Am. Chem. Soc., 1987, 109, 4261.
A. Yu. Tsivadze, Russ. Chem. Rev., 2004, 73, 5 [Usp. Khim., 2004, 73, 6].
A. G. Martynov, Y. G. Gorbunova, Inorg. Chim. Acta, 2007, 360, 122.
T. Toupance, V. Ahsen, J. Simon, J. Am. Chem. Soc., 1994, 116, 5352.
A. G. Martynov, I. V. Biryukova, Yu. G. Gorbunova, A. Yu. Tsivadze, Zh. Inorg. Khim., 2004, 49, 407 [Russ. J. Inorg. Chem. (Engl. Transl.), 2004, 49, 358].
O. Murillo, S. Watanabe, A. Nakano, G. W. Gokel, J. Am. Chem. Soc., 1995, 117, 7665.
I. P. Beletskaya, A. D. Averin, A. G. Bessmertnykh, F. Dënat, R. Guilard, Zh. Org. Khim., 2010, 46, 951 [Russ. J. Org. Chem. (Engl. Transl.), 2010, 46, 947].
M. V. Anokhin, A. D. Averin, A. K. Buryak, I. P. Beletskaya, Mendeleev Commun., 2011, 21, 132.
M. V. Anokhin, A. D. Averin, A. K. Buryak, I. P. Beletskaya, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 992 [Izv. Akad. Nauk, Ser. Khim., 2011, 968].
T. Ukai, H. Kawazura, Y. Ishii, J. J. Bonnet, J. A. Ibers, J. Organomet. Chem., 1974, 65, 253.
Author information
Authors and Affiliations
Corresponding author
Additional information
Based on the Materials of the XIX Mendeleev Congress on General and Applied Chemistry (September 25–30, 2011, Volgograd, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1459–1466, July, 2012.
Rights and permissions
About this article
Cite this article
Yakushev, A.A., Anokhin, M.V., Averin, A.D. et al. Palladium-catalyzed amination in the synthesis of aza- and diazacrown trismacrocyclic compounds. Russ Chem Bull 61, 1474–1482 (2012). https://doi.org/10.1007/s11172-012-0191-6
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-012-0191-6