Elsevier eBooks, Год журнала: 2024, Номер unknown, С. 91 - 149
Опубликована: Авг. 16, 2024
Язык: Английский
Organic Letters, Год журнала: 2024, Номер 26(12), С. 2381 - 2386
Опубликована: Март 15, 2024
Organic sulfones are an important class of chemical compounds widely used in many research fields. The direct decarboxylative sulfonylation carboxylic acids is attractive but challenging, particularly when iron as a metal catalyst. Herein, we describe photoinduced iron-catalytic method for the synthesis directly using via radical-based decarboxylation. This protocol mild, highly efficient, and easy-to-operate. A broad scope carbon electrophiles could be well tolerated. mechanism involving iron-catalyzed decarboxylation, radical transfer, single-electron reduction, nucleophilic attack proposed.
Язык: Английский
Процитировано
15
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Фев. 23, 2025
Trifluoromethyl enone emerges as a versatile and multifaceted building block in organic synthesis. A defluorinative heterocyclization reaction of readily available β,β-ditrifluoromethylated enones biocompatible sodium sulfinates has been developed for the modular synthesis densely functionalized furans with regio-defined C2,4-bissulfonyl C3-trifluoromethyl substitutions. This three-component method proceeds through sequential sulfonylation intramolecular O-cyclization, enabling assembly one furan ring, formation C-SO2/C–O bonds, cleavage three C(sp3)-F bonds one-pot manner under transition metal-free conditions. Moreover, obtained product can further react benzyne precursor to generate 1,4-epoxynaphthalene Diels–Alder cycloaddition. The is also distinguished by its broad substrate scope, excellent functional group tolerance, scalability.
Язык: Английский
Процитировано
1
Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1422 - 1429
Опубликована: Фев. 1, 2024
Abstract The photochemical catalyst‐free radical‐based synthesis of vinyl and 1,3‐dienyl sulfones is disclosed. Mechanistic investigations support that the transformations rely on a visible‐light‐promoted activation halogen‐bonding complex, which formed between an alkenyl (or 1,3‐dienyl) bromide sodium sulfinate salt. reactions exhibit wide functional group tolerance (compatible with heteroatoms, electron‐withdrawing electron‐donating groups), finding application in structural modification biologically relevant molecules. Eventually, continuous flow protocol was developed to upscale these transformations.
Язык: Английский
Процитировано
9
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(18), С. 5232 - 5277
Опубликована: Янв. 1, 2024
This review describes recent advances in the generation of aryl radicals using light and electricity. Such modern techniques allow for efficient energy resource utilization, thus providing more sustainable radical arylation methods.
Язык: Английский
Процитировано
8
Chemical Communications, Год журнала: 2024, Номер 60(56), С. 7228 - 7231
Опубликована: Янв. 1, 2024
A visible-light-induced K 2 S O 8 -promoted cascade sulfonation/cyclization reaction to afford a series of sulfonated quinolino[2,1- b ]quinazolinones has been developed under mild conditions.
Язык: Английский
Процитировано
4
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4619 - 4627
Опубликована: Март 27, 2024
Allyl sulfones are commonly present in bioactive compounds and organic building blocks. This work introduces a photocatalytic radical addition–elimination reaction involving readily accessible sulfonyl chlorides allyl bromides. It delivers structurally diverse allylic moderate to excellent yields, showcasing high tolerance functional groups. Notably, this method operates under mild conditions without the need for oxidants, stoichiometric reducing metals, or additives.
Язык: Английский
Процитировано
3
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Фев. 10, 2025
A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as reagents has been developed. Under the catalysis Pd(PPh3)4, a wide range γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild conditions, broad substrate scope, functional group tolerance, suitable for gram-scale synthesis.
Язык: Английский
Процитировано
0
Organic Chemistry Frontiers, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
A strategy to obtain 1,2-alkenyl ketone products by radical relay coupling is proposed.
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Июнь 3, 2025
We report photoinduced decarboxylative sulfonylation of carboxylic acids with sodium sulfinates for synthesizing sulfones. The reaction proceeds under mild conditions, directly utilizing without prefunctionalization, copper acetate as the oxidant and base at room temperature. This method demonstrates excellent substrate compatibility, accommodating simple acids, drug molecules successfully converted into corresponding Furthermore, we developed a two-step, one-pot protocol that integrated two DABSO (DABCO-bis(sulfur dioxide) adduct) to synthesize Biological activity evaluation revealed molecule-derived sulfones exhibited antiproliferative against tumor cells.
Язык: Английский
Процитировано
0
Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 366(1), С. 70 - 76
Опубликована: Ноя. 17, 2023
A strategy for sulfonylation of boronic acids with sulfonyl chlorides has been established via Suzuki-type radical cross-coupling. This approach allows the synthesis more than 50 sulfone examples enabled by photoredox catalysis under visible light radiation. Moreover, title reaction is applied in late-stage functionalization bioactive molecules, and further transformation resulting sulfones into 2-functionalized sulfones, borates, triphenylphosphine oxide N-arylcarbazole can be also achieved.
Язык: Английский
Процитировано
6