Alexei D. Averin

Diaminoanthraquinone-linked polyazamacrocycles: efficient and simple colorimetric sensor for lead ion in aqueous solution.

A new colorimetric molecular sensor based on a 1,8-diaminoanthraquinone signaling subunit exhibits efficient binding for lead ion in water and allows naked-eye detection.

Application of Pd-catalysed amines arylation for the synthesis of benzopolyazamacrocycles

Abstract Amination of 1,2- or 1,3-dihalobenzenes by linear polyamines in the presence of Pd(dba) 2 /BINAP catalytic system can serve as a convenient one-pot procedure for the synthesis of benzopolyazamacrocycles.

Synthesis of 1,8-bis(cyclam) and 1,8-bis(azacrown) substituted anthracenes by palladium-catalyzed arylation of cyclam

Abstract The Pd-catalyzed arylation of cyclam, cyclen, and azacrown ethers by aryl halides was studied. Cofacial biscyclam and bisazacrown were synthesized by direct bonding of the anthracenyl spacer to a nitrogen atom of macrocycles.

Synthesis of diazacrown ethers based on anthracene and anthraquinone by Pd-catalyzed amination reactions

Abstract Pd-catalyzed amination reactions of 1,8-dichloroanthracene and 1,8-dichloroanthra-9,10-quinone with di- and trioxadiamines can serve a convenient one-pot synthetic approach to diazacrown ethers.

Competitive addition and cycloaddition of low coordinated organophosphorus compounds to alkoxy- and aminoalkynes

Abstract Reactions of two- and three coordinated organophosphorus compounds with nucleophilic alkynes can proceed as competitive addition, [2+1]-, and [2+2]- cycloaddition reactions. Ring-chain tautomerism for phosphirenes and isomeric alkenylphosphines has been observed.

Synthesis of new tetraazamacrocycles by Pd-catalyzed amination of 1,8-dichloroanthracene and 1,8-dichloroanthra-9,10-quinone

Abstract Pd-catalyzed amination of 1,8-dichloroanthracene and 1,8-dichloroanthra-8,10-quinone leads to new tetraazamacrocycles containing anthracene or anthraquinone moiety.

Palladium-Catalyzed Amination of Dichloroquinolines with Adamantane-Containing Amines

Pd-catalyzed amination of isomeric 2,6-, 2,8-, 4,8- and 4,7-dichloroquinolines was studied using adamantane-containing amines in which substituents at the nitrogen atom differ in bulkiness. The selectivity of the amination of 2,6-dichloroquinoline was very low, substantially better results were obtained with 2,8-dichloroquinoline, and 4,8- and 4,7-dichloroquinolines provided the best yields of the amination products. Diamination of 4,8- and 4,7-dichloroquinolines was carried out with two amines which differ strongly in the bulkiness of the alkyl group. In the majority of cases BINAP ligand was successfully applied, however, it had to be replaced with DavePhos in certain reactions when using the most sterically hindered amine as well as for the diamination reactions.

New trends in the cross-coupling and other catalytic reactions

Abstract A mini-review covers the latest achievements in the field of metal-mediated cross-coupling reactions among which are palladium-catalyzed Heck, Suzuki, cyanation and amination reactions. The aspects of the application of Pd nanoparticles (PdNPs) are discussed. The possibilities of the applications of Cu(I)-catalyzed reactions are described. Special emphasis is made on the synthesis of polymacrocyclic compounds like porphyrin dyads and triads, polyazacryptands bearing fluorophore groups using catalytic methods. The application of Pd-catalyzed CH-activation reactions for porphyrin modifications is described, the use of Lewis acids catalysis and organocatalysis for enantioselective C–C bond formation is considered with the emphasis on the application of immobilized organocatalyst.

Oxaazamacrocycles incorporating the quinoline moiety: synthesis and the study of their binding properties towards metal cations

Novel dioxa- and trioxadiazamacrocycles have been synthesized by the Pd(0)-catalyzed amination of 4,6- and 4,7-dichloroquinolines with linear di- and trioxadiamines. Macrocyclization reaction was shown to be more successful for 4,6-dichloroquinoline, providing the corresponding macrocycles with yields of up to 32%. 4,6-Di(2-methoxyethylamino)quinoline was obtained in 88% yield for comparative studies. The synthesis of macrocycles comprising two 4,7-disubstituted quinoline moieties and two oxadiamine linkers has been accomplished. The binding properties of 4,6-diamino derivatives of quinoline have been studied with 17 metal cations using UV-vis and fluorescence spectroscopy. UV, fluorescence, and NMR spectral data demonstrated the formation of complexes of different compositions depending on the nature of the ligand and the metal cation. One of the macrocycles (5c) was shown to be applicable as a selective fluorescent and colorimetric chemosensor for Cu(II). Macrocyclic ligands 5 clearly showed a different behavior in the presence of metal cations compared to the non-cyclic derivative 10.

Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

Summary The Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines such as putrescine, cadaverine, spermine, spermidine and their homologues is described. Aryl iodides bearing electron-donating and electron-withdrawing groups have been employed in the study. The CuI/2-(isobutyryl)cyclohexanone/DMF catalytic system has found to be more efficient in the diarylation of diamines and spermine while the CuI/L-proline/EtCN system proved to be preferable for the diarylation of other tri- and tetraamines like spermidine, norspermidine and norspermine.