Russian Journal of Organic Chemistry, Год журнала: 2024, Номер 60(11), С. 2086 - 2107
Опубликована: Ноя. 1, 2024
Язык: Английский
Organic Letters, Год журнала: 2025, Номер 27(6), С. 1498 - 1503
Опубликована: Янв. 31, 2025
CuI/6-hydroxy picolinohydrazide-catalyzed coupling of (hetero)aryl chlorides with anilines proceeded well at 100 °C to afford biaryl amines in a diverse manner, which represents the first example Cu-catalyzed under milder conditions. The same catalytic system could make bromides work room temperature, giving corresponding products an excellent reaction scope.
Язык: Английский
Процитировано
1
Chemical Reviews, Год журнала: 2025, Номер unknown
Опубликована: Март 6, 2025
Cyclopropylamines are an important subclass of substituted cyclopropanes that combine the unique electronic and steric properties with presence a donor nitrogen atom. In addition to their in diverse array biologically active compounds, cyclopropylamines utilized as synthetic intermediates, particularly ring-opening or cycloaddition reactions. Consequently, synthesis these compounds has constituted significant research topic, evidenced by abundant published methods. widely used Curtius rearrangement, classical cyclopropanation methods have been adapted integrate function (Simmons-Smith reaction, metal-catalyzed reaction diazo on olefins, Michael-initiated ring-closure reactions) advances enantioselective synthesis. More recently, specific developed for preparation aminocyclopropane moiety (Kulinkovich reactions applied amides nitriles, cyclopropenes, involving C-H functionalization, ...). The topic this review is present different cyclopropylamine derivatives, aim covering methodological best possible, highlighting scope, stereochemical aspects future trends.
Язык: Английский
Процитировано
1
Molecules, Год журнала: 2025, Номер 30(3), С. 458 - 458
Опубликована: Янв. 21, 2025
An efficient method has been developed for the rapid production of diverse arrays 3,5-bis-aminated pyrazolo[1,5-a]pyrimidines. The utilizes CuI (5 mol%) and carbazole-based ligand L-1 (N-(9H-carbazol-9-yl)-1H-pyrrole-2-carboxamide) (10 Ullmann-type coupling various amines to 5-amino-3-bromopyrazolo[1,5-a]pyrimidine precursors after heating in diethylene glycol (DEG) only 1 h at 80 °C (microwave heating). 3,5-Bis-aminated products were obtained good excellent yields (60–93%, 83% average 29 examples). 1° 2° alkylamines, as well a variety aryl- or heteroarylamines coupled efficiently, alkyl (or aryl) C-5 tolerated. optimized conditions worked on both 50 mg 1.0 g scales gave two steps from commercially available 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine. Advantages provided by this include short reaction time, yields, broad substrate scope, avoidance toxic reagents commonly utilized reductive aminations C-3 NH2 substituted precursors.
Язык: Английский
Процитировано
0
Chemistry - A European Journal, Год журнала: 2025, Номер unknown
Опубликована: Янв. 30, 2025
Cyclopropane derivatives serve as important building blocks in organic synthesis, due to their three-membered stretched ring. Nitro-substituted cyclopropanes (NCPs) represent a special class of donor-acceptor (DACs) that contain strong electron-withdrawing nitro group substituent on the cyclopropyl moiety. Due versatile nature group, which can be converted into other functional azo groups or heterocyclic scaffolds, NCPs are considered design complex compounds. Herein, present review is organized two main sections focused synthesis and application NCPs. The part containing synthetic methodologies has been further divided distinct based mainly starting materials, such as: a) from nitroalkenes, b) nitro-bearing diazo compounds, c) nitroalkanes combination with alkenes, d) aminocyclopropanes under oxidative conditions, e) various through miscellaneous processes. In concerning applications use NCPs, categorization includes three subcategories, reduction 1-aminocyclopropane-1-carboxylic acids (ACC), ring opening leading valuable open-chain heterocycles, expansion larger cyclic
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Май 28, 2025
We present a novel copper-catalyzed method for aniline cross-couplings promoted by 6-hydroxy picolinhydrazide ligand. The achieves room-temperature reactivity with aryl bromides, enabled methanol/ethanol solvent mixture and mild, functional group-compatible base, catalyst loadings as low 0.5 mol %. use of industrially preferred solvents well the high catalytic activity, offers significant advancement in practicality scalability industrial processes. Furthermore, approach extends to cross-coupling chlorides under elevated temperatures demonstrates compatibility additional nucleophile classes.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2024, Номер 26(34), С. 7202 - 7206
Опубликована: Авг. 21, 2024
A Cu-catalyzed C–O coupling of (hetero)aryl chlorides with phenols at 120 °C on water was developed a designed ligand, N-(9H-carbazol-9-yl)picolinamide (L2). This method features good substrate scope (both electron-donating and electron-withdrawing), low catalyst/ligand loadings (down to 1 mol %), excellent scalability practicability.
Язык: Английский
Процитировано
2
Organic Process Research & Development, Год журнала: 2024, Номер unknown
Опубликована: Дек. 7, 2024
As the field of nonprecious metal catalysis continues to expand, we pursue a review series covering selected transformations in this area over short time interval highlight practical advancements. We seek raise awareness both current art and need continue development toward broader applications earth-abundant metals chemical pharmaceutical industries.
Язык: Английский
Процитировано
1
Russian Journal of Organic Chemistry, Год журнала: 2024, Номер 60(11), С. 2086 - 2107
Опубликована: Ноя. 1, 2024
Язык: Английский
Процитировано
0