The green chemistry paradigm in modern organic synthesis

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

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Palladium-Catalyzed Amination of Aryl Halides with Aqueous Ammonia and Hydroxide Base Enabled by Ligand Development

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(28), С. 19414 - 19424

Опубликована: Июль 5, 2024

The conversion of aryl halides to primary arylamines with a convenient and inexpensive source ammonia has been long-standing synthetic challenge. Aqueous would be the most least expensive form ammonia, but such palladium-catalyzed amination reaction high concentration water faces challenges concerning catalyst stability competing hydroxylation, reactions this practical reagent are rare. Further, amines conducted

Язык: Английский

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Discovery of the N–NHC Coupling Process under the Conditions of Pd/NHC- and Ni/NHC-Catalyzed Buchwald–Hartwig Amination

Organometallics, Год журнала: 2022, Номер 41(12), С. 1519 - 1531

Опубликована: Июнь 6, 2022

Complexes of palladium and nickel with N-heterocyclic carbene ligands (M/NHC, M = Pd, Ni) are widely used as effective catalysts for various amination reactions. A previously unaddressed transformation M/NHC complexes under typical conditions the Buchwald–Hartwig is disclosed. MII/NHC react primary aromatic aliphatic amines in presence strong bases to give azol-2(5)-imines M(0) species via a reductive elimination NHC azanide (N-deprotonated amine) ligands. Depending on structures azanide, N–NHC coupling can make significant contribution catalyst decomposition other reactions conducted bases. The discovery reaction has been shown be critically influenced by steric bulkiness N-substituents ligand. high an important factor suppressing deactivation pathway.

Язык: Английский

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Chemodivergent Dehydrogenative Coupling of Alcohols by 3d Metal Catalysts

ChemCatChem, Год журнала: 2024, Номер 16(12)

Опубликована: Фев. 19, 2024

Abstract Chemodivergent synthesis by transition metal catalysts is a straightforward and sustainable approach to achieving valuable organic compounds. Especially, the chemodivergent dehydrogenative couplings of alcohols with motifs develop various saturated unsaturated compounds are highly environmentally benign due reduced waste generation. In this concept review, we presented 3d (Mn, Fe, Co, Ni)‐catalyzed imines amines, carbonyl/alcohol compounds, nitriles, N ‐heterocycles, N‐/C‐alkylated indoles. The discussed reaction commanded two or three different products high chemoselectivity changing specific parameters, but keeping catalyst unchanged. Generally, acceptorless coupling (ADC) provides moieties, whereas borrowing‐hydrogen (BH) process results in

Язык: Английский

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Recent Advance in Electrochemical C(sp²)—H Amination of Arenes

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(3), С. 871 - 871

Опубликована: Янв. 1, 2024

Язык: Английский

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Synthesis of 5-(Aryl)amino-1,2,3-triazole-containing 2,1,3-Benzothiadiazoles via Azide–Nitrile Cycloaddition Followed by Buchwald–Hartwig Reaction

Molecules, Год журнала: 2024, Номер 29(9), С. 2151 - 2151

Опубликована: Май 6, 2024

An efficient access to the novel 5-(aryl)amino-1,2,3-triazole-containing 2,1,3-benzothiadiazole derivatives has been developed. The method is based on 1,3-dipolar azide–nitrile cycloaddition followed by Buchwald–Hartwig cross-coupling afford corresponding N-aryl and N,N-diaryl substituted 5-amino-1,2,3-triazolyl 2,1,3-benzothiadiazoles under NHC-Pd catalysis. one-pot diarylative Pd-catalyzed heterocyclization opens straightforward route triazole-linked carbazole-benzothiadiazole D-A systems. optical electrochemical properties of compound obtained were investigated estimate their potential application as emissive layers in OLED devises. quantum yield photoluminescence (PLQY) synthesized depends a large extent electron-donating strengths donor (D) component, reaching some cases values closed 100%. Based most photoactive derivative wide bandgap host material mCP, light-emitting layer was made. device showed maximum brightness 8000 cd/m2 at an applied voltage 18 V. current efficiency reaches value 3.29 cd/A.

Язык: Английский

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Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Апрель 3, 2025

Язык: Английский

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Access to amidines via C(sp²)–N coupling of trifluoroborate-iminiums with N-fluorobenzenesulfonimide

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Amidines are an important class of organic compounds with widespread application as superbases, nucleophilic catalysts, and building blocks heterocyclic in synthesis. Moreover, they represent structural motif medicinal chemistry. This work describes primary trifluoroborate-iminiums unprecedented azide- transition-metal-free transformation to N-sulfonyl amidines the presence N-fluorobenzenesulfonimide (NFSI). novel C(sp2)-N bond-forming reaction proceeds without excess any reagent, under mild conditions provides good high yields by a simple isolation procedure. Density functional theory (DFT) mechanistic studies into this support that use base is required activate either trifluoroborate-iminium or NFSI promote bond formation via attack nitrogen. The utility developed methodology showcased synthesis two bioactive compounds.

Язык: Английский

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Recent Achievements in the Copper-Catalyzed Arylation of Adamantane-Containing Amines, Di- and Polyamines

Catalysts, Год журнала: 2023, Номер 13(5), С. 831 - 831

Опубликована: Май 1, 2023

Rapid development of the copper-catalyzed amination aryl halides in beginning 21st century, known as Renaissance Ullmann chemistry, laid foundations for use this method a powerful tool construction C(sp2)-N bond and became rival Buchwald–Hartwig reaction. Various applications approach are well-documented number comprehensive more specialized reviews, overview form personal account Cu-catalyzed arylation heteroarylation adamantane-containing amines, di- polyamines, covers specific area, showing possibilities outlining general regularities, considering reagents structure, copper source ligands, scope, limitations. The material last decade is mainly considered, recent data on application unsupported nanoparticles Chan-Lam reaction an alternative to also discussed.

Язык: Английский

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Synthesis of 2,3-diphenylquinoxaline based diazapolyoxa- and polyazamacrocycles for AIE and sensing applications

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(25), С. 5181 - 5192

Опубликована: Янв. 1, 2024

Quinoxaline-based AIEgens with flexible receptor units were prepared using macrocyclization through the Pd-catalyzed amination reaction. They then used to prepare AIE-exhibiting test strips for measuring acidity in vapors and aqueous media.

Язык: Английский

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