Shining light on halogen-bonding complexes: a catalyst-free activation mode of carbon–halogen bonds for the generation of carbon-centered radicals

Chemical Science, Год журнала: 2023, Номер 14(21), С. 5545 - 5568

Опубликована: Янв. 1, 2023

This review provides a comprehensive overview on examples of how photochemical excitation halogen-bonding complexes can be useful for the generation carbon-centered radicals and their participation in synthetic organic transformations.

Язык: Английский

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Practical, scalable, and transition metal-free visible light-induced heteroarylation route to substituted oxindoles

Chemical Science, Год журнала: 2023, Номер 14(4), С. 897 - 902

Опубликована: Янв. 1, 2023

A novel photoinduced heteroarylation route to substituted oxindoles is disclosed.

Язык: Английский

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Physicochemical properties, drug likeness, ADMET, DFT studies, and in vitro antioxidant activity of oxindole derivatives

Computational Biology and Chemistry, Год журнала: 2023, Номер 104, С. 107861 - 107861

Опубликована: Март 31, 2023

Язык: Английский

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Photochemical Synthesis of Lactones, Cyclopropanes and ATRA Products: Revealing the Role of Sodium Ascorbate**

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Фев. 7, 2024

Abstract Light‐mediated processes have received significant attention, since they re‐surfaced unconventional reactivity platforms, complementary to conventional polar chemistry. γ‐Lactones and cyclopropanes are prevalent moieties, found in numerous natural products pharmaceuticals. Among various methods for their synthesis, light‐mediated protocols coming the spotlight, although these contingent upon use of photoorgano‐ or metal‐based catalysts. Herein, we introduce a novel photochemical activation iodo‐reagents via cheap sodium ascorbate ascorbic acid enable homolytic scission addition onto double bonds. The developed protocol was applied successfully formal [3+2] cycloaddition synthesis γ‐lactones, traditional atom transfer radical (ATRA) reactions one‐pot two‐step conversion alkenes cyclopropanes. In all cases, desired were obtained good high yields, while reaction mechanism thoroughly investigated. Depending on nature iodo‐reagent, halogen hydrogen‐bonded complex is formed, which initiates process.

Язык: Английский

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Synthesis of Vinyl and 1,3‐Dienyl Sulfones Enabled by Photochemical Excitation of Halogen‐Bonding Complexes

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

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Photochemical halogen-bonding assisted carbothiophosphorylation reactions of alkenyl and 1,3-dienyl bromides

Chemical Science, Год журнала: 2023, Номер 14(44), С. 12767 - 12773

Опубликована: Янв. 1, 2023

Herein, we present a synthetic procedure for the facile and general preparation of novel S-alkenyl dienyl phosphoro(di)thioates first time. Extensive mechanistic investigations support that reactions rely on photochemical excitation halogen-bonding complex, formed with phosphorothioate salt an alkenyl or bromide, which light-induced fragmentation leads to formation desired products through radical-based pathway. The substrate scope is broad exhibits wide functional group tolerance in final compounds, including molecules derived from natural products, all unknown potentially interesting biological properties. Eventually, very efficient continuous flow protocol was developed upscale these reactions.

Язык: Английский

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Organoselenium-Catalyzed Cross-Dehydrogenative Coupling of Alkenes and Azlactones

Organic Letters, Год журнала: 2022, Номер 24(9), С. 1780 - 1785

Опубликована: Фев. 28, 2022

The carbon–carbon bond-forming cross-dehydrogenative coupling of alkenes and azlactones by organoselenium catalysis involving a high-valent para-methoxyphenyl selenium species is disclosed. A series α,α-disubstituted α-amino acid derivatives were obtained in excellent regioselectivities through vinyl or allylic C–H functionalization. generality the method was elucidated cross-coupling an alkene with oxindole direct functionalization electron-rich arenes azlactones.

Язык: Английский

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Photo‐Catalyzed Redox‐Neutral 1,2‐Dialkylation of Alkenes

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(13), С. 2260 - 2265

Опубликована: Май 14, 2022

Abstract Difunctionalization of alkenes enables construction complex compounds in one pot. In this report, we presented an intermolecular, redox‐neutral three‐component dicarbofunctionalization activated under mild reaction conditions. The mechanistic studies indicated tertiary alkyl radicals from oxalate salts were first added to Giese‐type fashion, followed by nucleophilic addition with aldehydes produce the desired 1,2‐dialkylation products. catalyst system does not require any additives, good functional group compatibility, regioselectivity, and constructs two carbon centers simultaneously. magnified image

Язык: Английский

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Visible Light Induced Three‐Component 1,2‐Dicarbofunctionalization of Alkenes and Alkynes

The Chemical Record, Год журнала: 2023, Номер 23(11)

Опубликована: Июнь 12, 2023

Abstract Harnessing visible‐light in organic synthesis is one of the most effective methods that aligns with green and sustainable chemistry principles hence skyrocketed last two decades. Similarly, three‐component 1,2‐dicarbofunctionalization alkenes alkynes has recently been a great choice to construct complex molecular systems an easy rapid manner. Therefore, light‐induced reactions can be excellent alternative carry out reactions, very recently, chemists across globe have fascinated us their interesting articles. In this present review, we summarized recent advancements area visible light induced till March 2023. We categorized discussion based on catalysts used transformations for better understanding different important aspects these also covered.

Язык: Английский

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Frustrated-radical-pair-initiated atom transfer radical addition of perfluoroalkyl halides to alkenes

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(15), С. 3861 - 3869

Опубликована: Янв. 1, 2023

We employed a frustrated radical pair to catalyze the atom-transfer addition of perfluoroalkyl halides alkenes, which furnished series fluoroalkylated compounds in high regioselectivity and high-to-excellent product yields.

Язык: Английский

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