The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13263 - 13271
Опубликована: Сен. 6, 2024
Dihydroazepino[1,2-
Язык: Английский
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13263 - 13271
Опубликована: Сен. 6, 2024
Dihydroazepino[1,2-
Язык: Английский
Russian Chemical Reviews, Год журнала: 2023, Номер 92(12), С. RCR5104 - RCR5104
Опубликована: Дек. 1, 2023
After the appearance of green chemistry concept, which was introduced in vocabulary early 1990s, its main statements have been continuously developed and modified. Currently, there are 10–12 cornerstones that should form basis for an ideal chemical process. This review analyzes accumulated experience achievements towards design products processes reduce or eliminate use generation hazardous substances. The presents views leading Russian scientists specializing various fields this subject, including homogeneous heterogeneous catalysis, fine basic organic synthesis, electrochemistry, polymer chemistry, based on bio-renewable feedstocks energetic compounds materials. A new approach to quantitative evaluation environmental friendliness by authors is described. <br> bibliography includes 1761.
Язык: Английский
Процитировано
41Journal of the American Chemical Society, Год журнала: 2024, Номер 146(20), С. 13983 - 13999
Опубликована: Май 13, 2024
The reaction mechanism of Brønsted acid-catalyzed silane-dependent P═O reduction has been elucidated through combined computational and experimental methods. Due to its remarkable chemo- stereoselective nature, the acid/silane system widely employed in organophosphine-catalyzed transformations involving P(V)/P(III) redox cycle. However, full mechanistic profile this type yet be clearly established date. Supported by both DFT studies, our research reveals that likely proceeds mechanisms other than accepted "dual activation mode silyl ester" or "acid-mediated direct activation" mechanism. We propose although may vary with substitution patterns silane species, acid generally activates rather group transition structures. proposed differs significantly from associated traditional C═O reduction. uniqueness originates dominant Si/O═P orbital interactions structures P/H–Si interactions. comprehensive landscape provided us will serve as a guidance for rational design development more efficient systems well novel reactions
Язык: Английский
Процитировано
3Journal of the American Chemical Society, Год журнала: 2025, Номер unknown
Опубликована: Май 22, 2025
Tertiary phosphine is a powerful nucleophile that enables numerous synthetically important reactions. However, the exclusive reliance on two-electron pathway has restricted development of chemistry. We report here visible light photocatalytic phosphine-mediated deoxygenative [3 + 2] cycloaddition α,β-unsaturated carbonyls and activated alkenes, providing facile access to polysubstituted cyclopentenes from readily accessible starting materials in promising yields with good substrate scope. Mechanistic investigations corroborate transient involvement radical cation consequent α-addition (α electron-withdrawing groups) C-C double bonds due inherent electrophilicity cation, as opposed traditional nucleophilic β-addition phosphine. The ensuing single electron transfer reduction, Michael addition, 1,4-proton cascade furnish phosphorus ylide, which undergoes an intramolecular Wittig reaction finish construction cyclopentenes. This work demonstrates tertiary can serve convenient reagent for carbonyl deoxygenation act traceless directing group controllable cross-coupling two distinct new avenues expand frontiers chemistry synthetic
Язык: Английский
Процитировано
0Organic Letters, Год журнала: 2023, Номер 25(24), С. 4520 - 4524
Опубликована: Июнь 13, 2023
A highly enantioselective formal α-allylic alkylation of acrylonitrile is developed using 4-cyano-3-oxotetrahydrothiophene (c-THT) as a safe and easy-to-handle surrogate acrylonitrile. This two-step process consists an Ir(I)/(P,olefin)-catalyzed branched-selective allylic easily accessible branched rac-allylic alcohols the electrophile followed by retro-Dieckmann/retro-Michael fragmentation shown to be applicable for synthesis acrylates well acrolein.
Язык: Английский
Процитировано
7The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 12069 - 12073
Опубликована: Июль 27, 2023
A Rauhut-Currier reaction cascade is achieved in the presence of carbon nucleophiles under mild conditions. This original atom-economical transformation enables an efficient one-pot synthesis densely substituted carbocycles from readily accessible substrates. The key promoter role cesium cation process was demonstrated.
Язык: Английский
Процитировано
3Chemical Communications, Год журнала: 2023, Номер 59(78), С. 11720 - 11723
Опубликована: Янв. 1, 2023
We have disclosed a Rauhut-Currier reaction of γ-alkyl-substituted allenoate, catalyzed by L-valine-derived amide phosphine, to form trisubstitued which was trapped maleimide or DMAD via the Diels-Alder reaction. Exo-bicyclic succinimide derivatives including three continuous stereocenters with an exo-carbon-carbon double bound were constructed in up quantitative yields high stereospecificity.
Язык: Английский
Процитировано
2Опубликована: Май 11, 2023
A highly enantioselective formal α-allylic alkylation of acrylonitrile is developed using 4-cyano-3-oxotetrahydrothiophene (c-THT) as a safe and easy-to-handle surrogate acrylonitrile. This two-step process consists an Ir/(P,olefin)-catalyzed branched-selective allylic easily accessible branched rac-allylic alcohols the electrophile followed by retro-Dieckmann/retro-Michael fragmentation shown to be applicable for synthesis acrylates acrolein.
Язык: Английский
Процитировано
1Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(28), С. 5718 - 5723
Опубликована: Янв. 1, 2024
We describe the first phosphine-promoted intramolecular Rauhut-Currier reaction that triggers an Wittig process assembling new classes of diquinanes. The one-pot strategy provides ready access to simple diquinanes and various (hetero)arene-fused incorporated with up two contiguous all-carbon quaternary centers under metal-free neutral conditions. showcased generality method on a broad range substrates demonstrated its synthetic utility in accessing advanced intermediates relevant natural product synthesis material science.
Язык: Английский
Процитировано
0The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13263 - 13271
Опубликована: Сен. 6, 2024
Dihydroazepino[1,2-
Язык: Английский
Процитировано
0