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Pure Appl. Chem., 2004, Vol. 76, No. 9, pp. 1605-1619

Palladium-catalyzed arylation of linear and cyclic polyamines

I. P. Beletskaya and A. D. Averin

Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, Moscow 119992, Russia

Abstract: Synthetic protocols for the palladium-catalyzed arylation of various linear and cyclic polyamines and polyoxapolyamines has been worked out. Pd(0) and Pd(II)complexes with such phosphine ligands as dppf, BINAP, PPF-OMe, P(tBu)3,2-ditert-butylphosphino-1,1'-biphenyl have been explored in the catalytic amination reactions. Monoamination of chloro-, bromo-, and iodoarenes with di-, tri-, and tetraamines have been carried out, conditions for di- and polyarylation of linear polyamines have been elaborated. Successful arylation of 1,4,7,10-tetraazacyclododecane (cyclene) and 1,4,8,11-tetraazacyclotetradecane (cyclam) have been conducted. Intramolecular diamination of dihaloarenes such as 1,2-dibromobenzene, 2,6-dichlorobromobenzene, 1,3-dibromobenzene, 1,8-dichloroanthracene, 1,8-dichloroanthraquinone, 1,5-dichloroanthracene, and 1,5-dichloroanthraquinone afforded corresponding polyazamacrocycles containing arene moieties. For the first time, a convenient one-pot synthesis of the face-to-face arranged bismacrocyclic systems has been carried out.