Light-induced borylation: developments and mechanistic insights

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(20), С. 4397 - 4428

Опубликована: Янв. 1, 2021

This perspective delineates light-induced borylation methodologies, which have been developed in the last 10 years. Mechanistic insights explored throughout article for these UV- and visible-light-induced reactions.

Язык: Английский

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Organophotoredox‐Catalyzed Late‐Stage Functionalization of Heterocycles

Asian Journal of Organic Chemistry, Год журнала: 2021, Номер 10(8), С. 1848 - 1860

Опубликована: Май 14, 2021

Abstract In the last decade, visible light photoredox catalysis promoting radical‐based organic transformations has received enormous synthetic applicability, as they allow unfolding of site‐selective reactivities under mild reaction conditions. Moreover, utilizing dyes photocatalysts are attractive with regard to low cost, less toxicity, easy availability and high functional group tolerance. The organophotoredox‐catalyzed technologies enabling direct, efficient selective late‐stage functionalization various heterocycles leading formation C−C C−X (X=N, P, O, S, Se, Br) bonds have emerged at forefront methodologies available chemists. This minireview summarizes developments made in five years field governed by organophotocatalysts intends provide readers a comprehensive overview this research representative examples mechanistic insights.

Язык: Английский

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Photocatalytic transition-metal-free direct 3-alkylation of 2-aryl-2H-indazoles in dimethyl carbonate

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(13), С. 3286 - 3291

Опубликована: Янв. 1, 2021

A general transition-metal-free photocatalytic decarboxylative 3-alkylation reaction of 2-aryl-2H-indazoles was developed under visible-light irradiation mild conditions.

Язык: Английский

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Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(31)

Опубликована: Июль 22, 2022

Abstract The progress in C−N bond construction is significant synthetic and biological chemistry. Cross‐dehydrogenative couplings of C−H N−H motifs serve as a unique class the most atom‐economical straightforward strategies for constructing bonds. Herein, we enclosed updated methodologies developed assembly bonds via photo‐catalyzed, transition‐metal‐catalyzed, electrochemical, metal‐free amination amidation reactions saturated unsaturated Compared with well‐established transition‐metal‐catalyzed protocols, electricity, or visible light‐mediated are competent appealing. Plausible mechanistic pathways also described representative to provide insights future development environmentally kind processes.

Язык: Английский

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Recent advances in C–H functionalization of 2H-indazoles

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(39), С. 7746 - 7764

Опубликована: Янв. 1, 2022

2H-Indazoles are one class of the most important nitrogen-containing heterocyclic compounds. The 2H-indazole motif is widely present in bioactive natural products and drug molecules that exhibit distinctive bioactivities. Therefore, much attention has been paid to access diverse derivatives. Among them, late-stage functionalization 2H-indazoles via C-H activation recognized as an efficient approach for increasing complexity diversity In this review, we summarized recent achievements 2H-indazoles, including C3-functionalization through transition metal-catalyzed or a radical pathway, ortho C2'-H remote at benzene ring 2H-indazoles.

Язык: Английский

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CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(11), С. 1714 - 1755

Опубликована: Апрель 12, 2023

Abstract In the last decade, free radicals have found a wide application in functionalization of unsaturated compounds, such as alkenes, alkynes, and arenes, via free‐radical addition to carbon‐carbon π‐bonds. these processes, intermolecular attack on aromatic substrates represents challenge due relatively high resistance π‐system reactions comparison alkene C=C bonds. The heterocycles is especially interesting diversity their structures chemical properties well importance for medicinal chemistry, agrochemistry, materials science. Addition C‐centered widely known Minisci‐type well‐reviewed. this paper, we summarized main achievements less explored group processes: by heteroatom‐centered (O‐, N‐, S‐/Se‐, P‐radicals) with emphasis papers published after 2010. Literature analysis revealed strong trend towards usage electrochemistry photoredox‐catalysis generation recent years. remaining fundamental problem field lack experimental support proposed mechanisms frequent existence several plausible reaction pathways. progress mechanistic studies can significantly improve prediction optimal conditions depending structure.

Язык: Английский

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Electrochemically promoted C-3 amination of 2H-indazoles

Organic Chemistry Frontiers, Год журнала: 2020, Номер 8(4), С. 754 - 759

Опубликована: Дек. 11, 2020

A metal-free and external oxidant-free method for the C-3 amination of 2H-indazoles in good yields was developed under electrochemical conditions.

Язык: Английский

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Visible-Light-Induced Oxyalkylation of 1,2,4-Triazine-3,5(2H, 4H)-diones with Ethers via Oxidative Cross-Dehydrogenative Coupling

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(13), С. 8551 - 8561

Опубликована: Июнь 22, 2022

An efficient and convenient method to synthesize 6-oxyalkylated 1,2,4-triazine-3,5(2H, 4H)-diones has been developed via visible-light-induced cross-dehydrogenative coupling reaction between ethers with a wide range of functional group tolerance. The present transformation employs the cheap low-toxic 2-tert-butylanthraquinone as metal-free photocatalyst air green oxidant at room temperature. Moreover, this can also be driven by sunlight clean energy resource. synthetic utility is further demonstrated gram-scale application in preparation key intermediates bioactive molecules.

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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N‐Heteroarylation of Sulfonamides: An Overview

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(18), С. 3020 - 3043

Опубликована: Авг. 16, 2023

Abstract N ‐Heteroaryl sulfonamides are an extremely significant variety of organosulfur compounds that present in many FDA‐approved drugs and therapeutic agents. Therefore, synthesis these ‐heteroaryl is one the most interesting topics among synthetic organic chemists. Among various methodologies, direct C−N bond formation through ‐heteroarylation has emerged as a procedure continued choice it bypasses genotoxicity common traditional methods. This review encompasses summarizes progress development this subject with literature coverage up to June 2023.

Язык: Английский

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