Gennadij V. Latyshev

The nickel-catalyzed Sonogashira–Hagihara reaction

Abstract The Sonogashira–Hagihara coupling of terminal acetylenes with aryl iodides in the presence of a nickel catalyst and CuI was investigated. The reaction proceeds rapidly in aqueous dioxane in the presence of Ni(PPh 3 ) 2 Cl 2 with high yields of disubstituted tolanes being obtained. The reaction seems to be an inexpensive alternative to the palladium-catalyzed process.

Bis(ferrocenyl)mercury as a source of ferrocenyl moiety in Pd-catalyzed reactions of carbon-carbon bond formation

Abstract The application of bis(ferrocenyl)mercury as a source of ferrocenyl group in Pd-catalyzed reactions with aryl halides, acid chlorides and electrophilic alkynes has been demonstrated. The formation of dimethyl-(Z)-2,3-di(ferrocenyl)-2-butenedioate in Pd-catalyzed addition of bis(ferrocenyl)mercury to dimethylacetylenedicarboxylate has been confirmed by X-ray analysis.

Lewis and Brønsted acid induced (3 + 2)-annulation of donor-acceptor cyclopropanes to alkynes: indene assembly.

(3 + 2)-Annulation of donor-acceptor cyclopropanes to alkynes induced by both Lewis and Brønsted acids has been developed. The reaction provides a rapid approach to functionalized indenes displaying intense visible emission (λmax = 430 nm, Φ = 0.28-0.34).

The successive substitution of halogens in 4-chloro-6-iodoquinoline by aryl groups in cross-coupling reactions with arylboronic acids

Abstract The conditions for selective stepwise substitution of iodine and chlorine atoms in 4-chloro-6-iodoquinoline which allow the synthesis of the corresponding diarylquinolines with different aryl groups in the 4- and 6-positions, in a one-pot procedure, in high yields are reported. A significant effect of the addition of water or Bu 4 NBr on the rate and yield of both stages was discovered.

Palladium-catalyzed cross-coupling reaction of bis(ferrocenyl)mercury with aryl iodides

Abstract Cross-coupling reactions of bis(ferrocenyl)mercury with aryl- and heteroaryl iodides were shown to be easy and convenient for the synthesis of monoarylsubstituted ferrocenes in high yields. The highly selective substitution of iodine atom in iodobromoarenes by the ferrocenyl unit was demonstrated.

The chemoselective alkynylation of dihaloquinolines by the Sonogashira-Hagihara reaction

Conditions for the regioselective Sonogashira—Hagihara alkynylation of 4-chloro-6-iodo(bromo)quinolines were found and 6-alkynyl-4-chloroquinolines were obtained in 90—100% yields.

Successive substitution of halogen atoms in 4,6-dihaloquinolines in palladium-catalyzed reactions with amines and arylboronic acids

A procedure was developed for the synthesis of 4,6-diamino- and 4,6- or 6,4-arylaminoquinolines by palladium-catalyzed C-N- and/or C-C-cross-coupling of 6-bromo-4-chloroquinoline.

Pd-catalyzed alkylation of halogen-substituted steroids with organozinc compounds

A general procedure has been developed for the introduction of hydrophobic alkyl groups into positions 6, 3, and 17 of steroid molecules via palladium-catalyzed Negishi reaction of halogen-substituted steroids with benzyl- and alkylzinc halides.

Regioselective Hydrogenolysis of Donor–Acceptor Cyclopropanes with Zn-AcOH Reductive System

A convenient low-cost method for regioselective ring-opening of donor-acceptor cyclopropanes with the Zn-AcOH reductive system was developed. The general character of the method was displayed via efficient reduction of a representative series of 2-(het)arylcyclopropane-1,1-diesters as well as donor-acceptor cyclopropanes with other types of electron-withdrawing activating groups. This method opens a rapid access to γ-substituted propyl-1,1-diesters, ketoesters, cyanoesters, cyanoamides, dinitriles, etc., many of which are not readily accessible with alternative methods. The utility of the synthesized compounds was demonstrated by transforming them into valuable acyclic and cyclic compounds (including pharmacologically relevant carbazoles, δ-lactams, and oxindole derivatives).

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

Cu- and Pd-catalyzed arylation of aminocholanes has been described for the first time. While this Cu-catalyzed protocol provides high yields in reactions of aminocholanes with iodoarenes, Pd catalysis was found to be preferable for the reactions of aminocholanes with dichloroanthraquinones. UV–vis titration of bis(cholanylamino)anthraquinones with a series of cations demonstrated their high binding affinity to Cu2+, Al3+, and Cr3+.