The palladium-catalyzed amination was used to synthesize 2,7-diamino derivatives of naphthalene containing two chiral substituents and fluorophore groups (dansyl, 7-methoxycoumarin, 6,7-dimethoxycoumarin, 6-aminoquinoline). The synthesized compounds were studied by UV absorption and fluorescence spectroscopy in the presence of individual enantiomers of amino alcohols and salts of 21 metals. The possibility of using these compounds as fluorescent detectors for optically active compounds and metals was examined. In the presence of (S)-leucinol, the diquinoline derivative showed enhanced emission with a maximum at shorter wavelengths, which is not typical of its (R) isomer. This fact can be used for the recognition of these enantiomers. A number of naphthalene derivatives can be considered as potential fluorescent chemosensors for Cu(II)cations due to the total fluorescence quenching in the presence of this metal.

The palladium-catalyzed amination was used to synthesize optically active 3,3’-diaminosubstituted biphenyl derivatives (in particular, macrocyclic derivatives) decorated with additional fluorophore groups (dansyl and 7-methoxycoumarin). The synthesized compounds were studied by spectroscopic methods (UV spectroscopy, fluorescence) in the presence of individual enantiomers of amino alcohols and metal salts. One of the synthesized compounds was demonstrated to serve as an enantioselective fluorescent detector for enantiomers of 2-amino-1-propanol because of different changes in the fluorescence spectra. Certain compounds can be used as molecular probes for the detection of Cu II , Al III , Cr III , and In III cations due to characteristic changes in the fluorescence spectra upon the addition of metal perchlorates.

A series of optically active macrobicyclic cryptands were obtained by the Pd 0 -catalyzed amination reaction between ( S )-2,2′-diamino-1,1′-binaphtalene (BINAM) and N , N′ -bis-(bromobenzyl) derivatives of diaza-crown ethers. The dependence of yields of the macrobicyclic products on the structure of the diaza-crown ether derivatives was demonstrated. A comprehensive study of the effects of a number of optically active amino alcohols on the fluorescence spectra of the prepared compounds was carried out.

Amination of 3,6-dichloropyridazine, chloropyrazine, 2,3and 2,6-dichloropyrazines, 2-chloroquinoxaline, 1-chloroand 1,3-dichloroisoquinolines with various adamantane-containing amines characterized by different steric hindrances at the amino group was studied. The yields of the amination products depended on the structure of starting compounds. In the reactions of all the dichloroheteroarenes, selective substitution of only one chlorine atom took place, with the best yields being observed for 2,6-dichloropyrazine. In the reaction of 1,3-dichloroisoquinoline, the chlorine atom at position 1 was selectively substituted in up to 90% yield.

Catalyst-free reactions of 2-fluoropyridine with amines and diamines bearing the adamantyl moiety at either the N atom or in the side chain were studied. Amines, which do not contain secondary alkyl substituents at the amino group, react with an excess of 2-fluoropyridine to give N -(pyridin-2-yl) derivatives in the yields from moderate to good. 2-Fluoro-5-halopyridines were found to be more reactive than 2-fluoropyridine.

Palladium-catalyzed arylation of diverse amines of the adamantane series with isomeric chloroquinolines was investigated. The 2-chloroquinoline is the most reactive, however the best yields of the N-arylation products are most frequently obtained in the reaction with the less reactive 6-chloroquinoline. The applicability of the reaction is limited by the size of the substituent at the amino group. In some instances the noncatalytic amination of chloroquinolines was possible.