Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(8), С. 2070 - 2074
Опубликована: Янв. 1, 2023
Acid-catalyzed disulfuration and rearrangement have been disclosed for the construction of alkynyl or acyl disulfides from thiols N -alkynylthio phthalimides, enabling access to disulfide-modified thiodrugs, thiopeptides thioglycosides.
Язык: Английский
Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(3)
Опубликована: Ноя. 28, 2023
Abstract A general one‐pot approach to diverse N ‐acylsulfenamides from a common S ‐phenethylsulfenamide starting material is reported. This was demonstrated by C−S bond formation utilizing commercially abundant (hetero)aryl iodides and boronic acids provide sulfilimine intermediates that undergo thermal elimination of styrene. In contrast, all prior approaches rely on thiol inputs introduce sulfenamide ‐substituents. broad scope reaction including for approved drugs drug precursors with dense display functionality. Several different types sulfur functionalization were performed derived complex precursor the blockbuster anticoagulant apixaban, highlighting utility this introduction high oxidation state groups in bioactive compounds. Mechanistic studies established key styrene step proceeds concerted does not require reagents or catalysts, therefore, should be applicable synthesis electrophiles conditions formation.
Язык: Английский
Процитировано
11
Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(3), С. 830 - 835
Опубликована: Дек. 19, 2023
Nickel-catalyzed C–SS reductive cross-coupling reaction of dithiosulfonate and unactivated alkyl halides for producing unsymmetric disulfides with broad substrate scope under mild conditions excellent functional group tolerance.
Язык: Английский
Процитировано
11
Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(5)
Опубликована: Дек. 7, 2023
A mechanochemical synthesis of sulfonimidamides by iron(II)-catalyzed exogenous ligand-free N-acyl nitrene transfer to sulfinamides is reported. The one-step method tolerates a wide range with various substituents under solvent-free ambient conditions. Compared its solution-phase counterpart, this approach shows better conversion and chemoselectivity. Mechanistic investigations ESI-MS revealed the generation crucial iron intermediates.
Язык: Английский
Процитировано
10
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2561 - 2565
Опубликована: Янв. 1, 2024
A nitrene transfer reaction of nitrosobenzenes with N -acyloxyamides using FeCl 2 ·4H O as a cheap and commercially available catalyst was developed for facile synthesis -acyl azoxy compounds high functional-group compatibility.
Язык: Английский
Процитировано
4
Chemical Communications, Год журнала: 2023, Номер 59(47), С. 7247 - 7250
Опубликована: Янв. 1, 2023
A visible-light-induced radical cascade heteroarene-migratory dithiosulfonylation has been developed to synthesize polysulfides, which can be transformed into dihydrothiophene and homoallyl disulfide derivatives.
Язык: Английский
Процитировано
9
Green Chemistry, Год журнала: 2023, Номер 25(19), С. 7529 - 7533
Опубликована: Янв. 1, 2023
The visible-light-promoted iron-catalyzed S–N cross coupling of thiols with dioxazolones is described. This reaction occurred via an exogenous-photosensitizer-free process and showed wide substrate scope under mild conditions.
Язык: Английский
Процитировано
9
Nature Communications, Год журнала: 2025, Номер 16(1)
Опубликована: Янв. 2, 2025
Unsymmetric disulfides are prevalent in natural products and essential medicinal chemistry materials science, but their robust synthesis poses significant challenges. In this paper, we report an expeditous transition-metal-free methodology for synthesizing unsymmetric through the addition of perthiyl radicals to alkenes. This study marks use generating by reacting SO2 with unactivated alkyl (pseudo)halides (Cl/Br/I/OTs). Various primary, secondary tertiary substituted different functional groups successfully function as suitable reactants. The formation involvement reaction process verified mechanistic studies DFT calculations. Overall, method leverages readily available electrophiles alkenes alongside a single setup efficiently form both carbon-sulfur sulfur-sulfur bonds simultaneously. Here, authors novel transition-metalfree
Язык: Английский
Процитировано
0
Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 200 - 216
Опубликована: Янв. 22, 2025
Over the past decade, dioxazolones have been widely used as N -acylamide sources in amidation processes of challenging substrates, typically employing precious transition metals. However, these catalytic systems often present several challenges associated with cost, toxicity, stability, and recyclability. Among 3d metals, copper catalysts gaining increasing attention owing to their abundance, cost-effectiveness, sustainability. Recently, applied chemical transformation dioxazolones, conferring a convenient protocol towards amidated products. This review highlights recent advancements synthetic transformations particular examples salts.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Фев. 27, 2025
The functionalization of N-acylsulfenamides is a research focus in organosulfur chemistry, as the N-S array has unique properties and versatile applications. Although great progress been made S-functionalization, N-functionalization, especially N-arylation N-acylsulfenamides, rarely explored because lower nucleophilicity N-site. Herein, we report Brønsted acid-catalyzed regioselective reaction with o-quinone diimides. Under mild metal-free conditions, wide range N-arylated have prepared good yields excellent regioselectivity. ease gram-scale synthesis transformations into useful sulfonamides demonstrates their synthetic practicality.
Язык: Английский
Процитировано
0
Chemical Science, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
A nitrene-mediated aminative N–N–N coupling enables direct triazene 1-oxide synthesis via an aminonitrene–nitrosoarene pathway.
Язык: Английский
Процитировано
0