Visible light-induced organophotoredox-catalyzed difunctionalization of alkenes and alkynes

Green Chemistry, Год журнала: 2023, Номер 25(21), С. 8459 - 8493

Опубликована: Янв. 1, 2023

This review comprehensively summarizes visible light-induced difunctionalization strategies for alkene and alkyne systems in metal-free conditions with literature coverage up to July 2023.

Язык: Английский

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The role of silicon in drug discovery: a review

RSC Medicinal Chemistry, Год журнала: 2024, Номер 15(10), С. 3286 - 3344

Опубликована: Янв. 1, 2024

This review aims to highlight the role of silicon in drug discovery.

Язык: Английский

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Copper‐Catalyzed Radical Silylarylation of Activated Alkenes: Preparation of β‐Silyl Amide‐Pharmaceutical Hybrids

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1325 - 1330

Опубликована: Фев. 2, 2024

Abstract Copper‐catalyzed silylarylation of N ‐(arylsulfonyl)acrylamides via a tandem silyl radical addition/1,4‐aryl migration/desulfonylation sequence has been developed. This method employs silanes as the precursor and di‐ tert ‐butyl peroxide (DTBP) initiator. By using this cascade procedure, series β ‐silyl amide‐pharmaceutical hybrids which contain an α ‐all‐carbon quaternary stereocenter were facilely synthesized.

Язык: Английский

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Modular access to alkylgermanes via reductive germylative alkylation of activated olefins under nickel catalysis

Nature Communications, Год журнала: 2023, Номер 14(1)

Опубликована: Ноя. 23, 2023

Abstract Carbon-introducing difunctionalization of C-C double bonds enabled by transition-metal catalysis is one most straightforward and efficient strategies to construct C-X concurrently from readily available feedstocks towards structurally diverse molecules in step; however, analogous for introducing germanium group other functionalities remains elusive. Herein, we describe a nickel-catalyzed germylative alkylation activated olefins with easily accessible primary, secondary tertiary alkyl bromides chlorogermanes as the electrophiles form C-Ge simultaneously. This method provides modular facile approach synthesis broad range alkylgermanes good functional compatibility, can be further applied late-stage modification natural products pharmaceuticals, well ligation drug fragments. More importantly, this platform enables expedient substituted ospemifene-Ge-OH, which shows improved properties compared ospemifene treatment breast cancer cells, demonstrating high potential our protocol development.

Язык: Английский

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Nickel-Catalyzed Reductive Cross-Coupling of Propargylic Acetates with Chloro(vinyl)silanes: Access to Silylallenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 2885 - 2894

Опубликована: Фев. 14, 2024

Because of their various reactivities, propargyl acetates are refined chemical intermediates that extensively applied in pharmaceutical synthesis. Currently, reactions between and chlorosilanes may be the most effective method for synthesizing silylallenes. Nevertheless, owing to adaptability selectivity substrates, transition metal catalysis is difficult achieve. Herein, nickel-catalyzed reductive cross-coupling substituted vinyl synthesis tetrasubstituted silylallenes described. Therein, metallic zinc a crucial reductant effectively enables two electrophilic reagents selectively construct C(sp2)–Si bonds. Additionally, Ni-catalyzed mechanism involving radical process proposed on basis deuteration-labeled experiments.

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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Photoredox/Nickel Dual-Catalytic Asymmetric Silylarylation of Alkenes

Organic Letters, Год журнала: 2025, Номер 27(2), С. 680 - 685

Опубликована: Янв. 6, 2025

The efficient construction of chiral aryl-containing organosilicon frameworks via catalytic enantioselective three-component silylarylation alkenes remains a great challenge. Herein, photoredox/nickel dual-catalytic asymmetric protocol has been disclosed by using biimidazoline (BiIM) as the ligand, silylboranes silyl radical precursors, aryl bromides coupling partners, and morpholine promoter. Remarkably, reaction features mild green conditions, high efficiency, excellent enantioselectivity, enabling facile synthesis valuable tropic acid sila-isoflavanone structures.

Язык: Английский

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Electrochemical-induced hydrofunctionalizations of alkenes and alkynes

Chemical Synthesis, Год журнала: 2024, Номер 4(1)

Опубликована: Март 1, 2024

The hydrofunctionalizations of readily available alkenes and alkynes are one the most effective useful routes to afford diverse value-added compounds. Although traditional hydrofunctionalization strategies catalyzed by metal catalysts present convenient approaches, they also accompanied resource consumption environmental crisis. Electrosynthesis, as a renewable sustainable technology, has become cost- atom-efficient synthetic route. In this review, electrochemical-induced summarized presented. each section, electrochemical strategy access hydrogenation other (hydroboration, hydrosilylation, hydroalkylation, hydroalkoxylation, hydrocyanation, hydrocarboxylation, etc. ) products elaborated in detail separately. Finally, current challenges prospects for unsaturated carbon‒carbon (C‒C) bonds discussed briefly.

Язык: Английский

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Ligand-modulated nickel-catalyzed regioselective silylalkylation of alkenes

Nature Communications, Год журнала: 2023, Номер 14(1)

Опубликована: Ноя. 23, 2023

Organosilicon compounds have shown tremendous potential in drug discovery and their synthesis stimulates wide interest. Multicomponent cross-coupling of alkenes with silicon reagents is used to yield complex silicon-containing from readily accessible feedstock chemicals but the reaction simple remains challenging. Here, we report a regioselective silylalkylation alkenes, which enabled by using stable Ni(II) salt an inexpensive trans-1,2-diaminocyclohexane ligand as catalyst. Remarkably, this can tolerate broad range olefins bearing various functional groups, including alcohol, ester, amides ethers, thus it allows for efficient selective assembly diverse bifunctional organosilicon building blocks terminal alkyl halides Suginome reagent. Moreover, expedient synthetic route toward alpha-Lipoic acid has been developed methodology.

Язык: Английский

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Photocatalytic selective 1,4-oxyimination/diamination across C=C and N=N bonds to access structurally diverse N-N-N triazane derivatives

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Авг. 1, 2024

A highly selective and atom-economical multi-component remote difunctionalization strategy has been successfully developed. This utilizes precise control over the radical properties of bifunctional precursors electronic traits olefins diazenes to achieve effective radical-mediated 1,4-oxyimination/diamination across C=C N=N bonds. By capitalizing on compatibility reactivity tuning, this approach enables synthesis complex triazine compounds with an N-N-N framework, providing a versatile tool for constructing diverse molecular structures. metal-free method is atom-efficient adaptable various substrates, demonstrating remarkable tolerance broad range functional groups.

Язык: Английский

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