Chemical Science, Год журнала: 2024, Номер unknown
Опубликована: Дек. 24, 2024
The readily available alkyl triflimidate reagent NTf2 has been used for deaminative C–B, C–S, C–Se, and C–Te bond formations. This protocol could be applied to a variety of transformations, demonstrating its potential primary amine functionlization.
Язык: Английский
Journal of the American Chemical Society, Год журнала: 2024, Номер 146(40), С. 27583 - 27593
Опубликована: Сен. 26, 2024
The exploration of strong chemical bonds as synthetic handles offers new disconnection strategies for the synthesis functionalized molecules via transition metal catalysis. However, slow oxidative addition rate these covalent to a center hampers their utility. Here, we report C(sp
Язык: Английский
Процитировано
8
Organic Letters, Год журнала: 2025, Номер 27(2), С. 583 - 587
Опубликована: Янв. 7, 2025
The functionalization of the C–N bond amines is a straightforward strategy for construction complex scaffolds or late-stage pharmaceuticals. Herein, we describe photoredox-catalyzed deaminative alkylation primary amine-derived isonitriles that provides unnatural amino acid derivatives under mild conditions. use silacarboxylic acids as silyl radical precursors enables generation carbon-centered radicals allow Csp3–Csp3 bonds via Giese-type addition, avoiding undesired hydrodeamination product.
Язык: Английский
Процитировано
1
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(47)
Опубликована: Авг. 10, 2024
Abstract The functionalization of pyridines is crucial for the rapid construction and derivatization agrochemicals, pharmaceuticals, materials. Conventional approaches have primarily focused on ortho ‐ para ‐positions, while achieving precise meta‐selective functionalization, particularly at C5 position in substituted pyridines, remains a formidable challenge due to intrinsic electronic properties pyridines. Herein, we present new strategy meta C5‐selective C−H sulfonylation N ‐amidopyridinium salts, which employs transient enamine‐type intermediate generated through nucleophilic addition salts. This process harnesses power electron donor‐acceptor complexes, enabling high selectivity broad applicability, including complex bearing valuable sulfonyl functionalities under mild conditions without need an external photocatalyst. remarkable selectivity, combined with applicability late‐stage significantly expands toolbox pyridine unlocking access previously unattainable ‐sulfonylated
Язык: Английский
Процитировано
4
Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155573 - 155573
Опубликована: Апрель 1, 2025
Язык: Английский
Процитировано
0
ChemSusChem, Год журнала: 2024, Номер unknown
Опубликована: Июнь 8, 2024
Abstract A convenient and sustainable method for synthesizing sulfonyl‐containing compounds through a catalyst‐free aqueous‐phase hydrosulfonylation of alkenes alkynes with sulfonyl chlorides under visible light irradiation is presented. Unactivated alkenes, electron‐deficient alkyl aryl can be hydrosulfonylated various at room temperature excellent yields geometric selectivities by using tris(trimethylsilyl)silane as hydrogen atom donor silyl radical precursor to activate chlorides. Mechanistic studies revealed that the photolysis in aqueous solution produce crucial success this reaction.
Язык: Английский
Процитировано
3
Organic Letters, Год журнала: 2024, Номер 26(24), С. 5172 - 5176
Опубликована: Июнь 12, 2024
Herein we report silyl radicals serve as isocyanide transfer agents for Giese-type reaction from aliphatic amines and electron-deficient olefins. α-Primary, α-secondary, sterically encumbered α-tertiary primary could be easily converted into isocyanides coupling with olefins by employing latent under visible light irradiation. Notably, the abstraction of silane-mediated not only enables voltage-independent activation strong C-N bonds but also represents a mechanistic alternative in which single electron reduction protonation processes are replaced direct hydrogen atom transfer. This transformation occurs photoinduced catalyst-free conditions exhibits excellent functional group compatibility mild conditions.
Язык: Английский
Процитировано
2
Опубликована: Авг. 8, 2024
Photoredox catalysis has become an invaluable tool for the construction of organic molecules, allowing unparalleled control over radical intermediates enabled by mild conditions achieved through visible-light activation a photocatalyst. These reactions can be classified under two distinct mechanistic paradigms: closed photocatalytic cycles, and photoinitiated chain reactions. While optimization strategies each these classes reaction differ significantly, chemists still lack straightforward means probing chain-propagation. In this work, we report simple accessible approach to performing intermittent illumination studies characterizing in photoredox catalysis. Using modern LED technologies precisely rate sample illumination, were able validate presence product-forming three previously reported protocols. Furthermore, technique also allows determination chain-propagating lifetimes graphical analysis. Given operational simplicity ease accessibility, believe will great value practitioners field moving forward.
Язык: Английский
Процитировано
2
ACS Catalysis, Год журнала: 2024, Номер 14(23), С. 17286 - 17292
Опубликована: Ноя. 8, 2024
Herein, we demonstrate the ability of isonitriles to be used as alkyl radical precursors in a photoredox-catalyzed transformation involving selective C-N cleavage and Csp
Язык: Английский
Процитировано
2
Organic Letters, Год журнала: 2024, Номер unknown
Опубликована: Ноя. 25, 2024
Reductive radical generation has become a cornerstone of modern photoredox chemistry. However, the synthesis functionalized precursors remains tedious multistep process. In this study, we focus on potential nitro group as redox-active functional and present denitrative alkenylation nitroalkanes, facilitated by photoreductive alkyl radicals from nitroalkanes. By taking advantage facile α-functionalization successfully generate various radicals, which are subsequently used in reactions.
Язык: Английский
Процитировано
2
Chemical Science, Год журнала: 2024, Номер 15(35), С. 14188 - 14194
Опубликована: Янв. 1, 2024
A photoredox catalytic strategy has been developed to enable the functionalization of a variety commercially available, structurally different radical precursors by use bench-stable isonitrile as an efficient cyanating reagent. Specifically, radical-based reaction provided mild and convenient procedure for cyanation primary, secondary tertiary radicals derived from widely accessible sp
Язык: Английский
Процитировано
1