Journal of Catalysis, Год журнала: 2023, Номер 427, С. 115098 - 115098
Опубликована: Авг. 19, 2023
Язык: Английский
Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(16), С. 4388 - 4393
Опубликована: Янв. 1, 2022
The synthesis of 3-trifluoromethylisoquinolinones by a ruthenium( ii )-catalyzed C–H activation/annulation reaction benzoic acids and CF 3 -imidoyl sulfoxonium ylides has been achieved.
Язык: Английский
Процитировано
42
Journal of the American Chemical Society, Год журнала: 2023, Номер 145(15), С. 8417 - 8429
Опубликована: Март 23, 2023
Mechanistic understanding of asymmetric induction plays a crucial role in designing new catalytic reactions. Reported herein is atroposelective access to C-N axially chiral isoquinolones via rhodium-catalyzed C-H activation N-alkoxy benzamides and annulation with imidoyl sulfoxonium ylides. The coupling system proceeded excellent functional group tolerance, different conditions were identified afford one or the other enantiomeric product each enantioselectivity for representative class ylide reagent, thus making both enantiomers readily available using same catalyst. Experimental computational studies revealed pathway alkylation enantio-determining formal nucleophilic substitution-C-N cyclization that mediated by rhodium catalyst σ-bond metathesis as mechanism. Computational indicated solvent-dependent enatiodivergence originated from levels neutral versus cationic species.
Язык: Английский
Процитировано
40
Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(31), С. 6246 - 6276
Опубликована: Янв. 1, 2024
Recent advances in the preparation of trifluoromethyl-containing heterocyclics via trifluoromethyl building block strategies over period from 2019 to present are systematically summarized and discussed.
Язык: Английский
Процитировано
10
Organic Letters, Год журнала: 2024, Номер 26(1), С. 62 - 67
Опубликована: Янв. 3, 2024
We have found a chameleonic reactivity of imidoyl sulfoxonium ylides. On the one hand, ylides react with electron-deficient reagents, such as alkynyl esters, to lead formation 1,2-dihydro-pyridines. The methyl group attached sulfur atom acts methylene donor. other pyridinium 1,4-zwitterionic thiolates, which leads functionalized pyrroles. Both transformations feature mild reaction conditions and good functional tolerance.
Язык: Английский
Процитировано
9
Organic Letters, Год журнала: 2022, Номер 24(40), С. 7288 - 7293
Опубликована: Окт. 4, 2022
A ruthenium-catalyzed peri-selective C-H activation and annulation of 1-naphthols with CF3-substituted imidoyl sulfoxonium ylides that uses hydroxyl as a weakly coordinating directing group is disclosed. The strategy provides facile practical route to diverse trifluoromethyl-containing 2,3-dihydrobenzo[de]chromen-2-amines high efficiency. Notable advantages this protocol include readily available materials, excellent regioselectivity, good functional compatibility, scalability.
Язык: Английский
Процитировано
34
Organic Letters, Год журнала: 2022, Номер 24(48), С. 8864 - 8869
Опубликована: Дек. 1, 2022
An efficient and straightforward approach for the synthesis of trifluoromethyl-decorated benzo[de][1,8]naphthyridines has been achieved via Rh(III)-catalyzed dual C-H activation cascade annulation benzimidates CF3-imidoyl sulfoxonium ylides. The novel transformation involves formation four new chemical bonds along with release two molecules dimethyl sulfoxide (DMSO) one molecule each ethanol amine. optoelectronic properties obtained fused aromatic products have investigated by recording UV-vis absorption emission spectra.
Язык: Английский
Процитировано
33
Organic Letters, Год журнала: 2022, Номер 24(37), С. 6822 - 6827
Опубликована: Сен. 9, 2022
A straightforward strategy for the metal-free construction of trifluoromethyl-containing pyrazole derivatives has been achieved from readily available α-halo hydrazones and CF3-imidoyl sulfoxonium ylides. The cascade transformation proceeds through formal [4+1] cycloaddition followed by an unexpected dual double bond isomerization. protocol features mild conditions, easy operation, excellent substrate compatibility, good regioselectivity. synthetic utility is demonstrated scale-up reaction further elaboration obtained products.
Язык: Английский
Процитировано
30
Chemical Communications, Год журнала: 2023, Номер 59(33), С. 4872 - 4890
Опубликована: Янв. 1, 2023
Recent advances in the direct synthesis of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides (TFAICs) and derivatives, including trifluoroacetimidohydrazides (TFAIHs) CF3-imidoyl sulfoxonium ylides (TFISYs), are systematically summarized discussed. The cascade annulation reactions synthons with suitable coupling partners have emerged as a powerful promising tool for construction variety trifluoromethyl-substituted heterocycles. Compared other building blocks, TFAICs derivatives notable merits easy availability handling, relative stability safety, high reactivity.
Язык: Английский
Процитировано
22
Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(15), С. 3843 - 3848
Опубликована: Янв. 1, 2023
We have developed a Rh( iii )-catalyzed C–H activation/chemodivergent annulation of N -carbamoylindoles with TFISYs, allowing facile access to variety trifluoromethyl-substituted (dihydro)pyrimidoindolones high efficiency. Solvents play critical role in the selectivity reaction.
Язык: Английский
Процитировано
22
Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(9), С. 1521 - 1525
Опубликована: Март 31, 2023
Abstract An approach for the construction of 5‐trifluoromethyl‐1,4‐dihydro‐1,2,4‐triazines has been developed via base‐mediated [3+3] cycloaddition in‐situ generated nitrile imines and CF 3 ‐substituted imidoyl sulfoxonium ylides. The metal‐free protocol is characterized by readily available starting materials, mild conditions, a broad substrate scope, high efficiency, good synthetic prospect, scalability. magnified image
Язык: Английский
Процитировано
17