Direct decarboxylative Giese reactions

Chemical Society Reviews, Год журнала: 2022, Номер 51(4), С. 1415 - 1453

Опубликована: Янв. 1, 2022

This review summarizes recent progress on using carboxylic acids directly as convenient precursors for the 1,4-radical conjugate addition (Giese) reaction.

Язык: Английский

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Mn-Catalyzed Electrochemical Radical Cascade Cyclization toward the Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one Derivatives

ACS Catalysis, Год журнала: 2020, Номер 10(12), С. 6676 - 6681

Опубликована: Май 29, 2020

Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives are prevalent in many synthetic intermediates, pharmaceuticals, and organic materials. Herein, we develop a Mn-catalyzed electrochemical radical cascade cyclization reaction that uses electricity as the primary energy input to promote reaction, leading series of benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one under exogenous-oxidant-free conditions. It is worth noting this method can not only realize synthesis but also provides new strategy for generating alkyl radicals from alkylboronic acids.

Язык: Английский

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Progress in Photoinduced Radical Reactions using Electron Donor‐Acceptor Complexes

Asian Journal of Organic Chemistry, Год журнала: 2021, Номер 10(4), С. 711 - 748

Опубликована: Фев. 11, 2021

Abstract Photocatalyzed organic synthesis transformation is a remarkable green synthetic strategy because of the advantages operational simplicity, high chemoselectivities, cheap, and environmental benignancy, along with extensive applications in fields organic, pharmaceutical functional material chemistry. Generally, photoredox catalysts or photosensitizers are necessary for generation their excited states to perform successive oxidative reductive reactions through single electron transfer (SET) energy (ET) process. Furthermore, exploration colored donor‐acceptor (EDA) complex charge (CT) between an electron‐rich electron‐poor substrate provides chance deliver intermediate under irradiation light, resulting formation radical activate species induce various reactions. These were performed without need any external photocatalysts mild reaction conditions. Herein, this review focuses on recent progress photoinduced addition reactions, borylations, radical‐radical cross‐coupling degradation cascade cyclization via EDA complexes. We highlight these novel methodologies applications, as well mechanisms. This will help provide references medicinal chemists who charmed by photochemical transformations based

Язык: Английский

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Visible-Light Induced Radical Perfluoroalkylation/Cyclization Strategy To Access 2-Perfluoroalkylbenzothiazoles/Benzoselenazoles by EDA Complex

Organic Letters, Год журнала: 2019, Номер 21(11), С. 4019 - 4024

Опубликована: Май 17, 2019

A novel and practical fluoroalkyl radical-initiated cascade reaction was developed to access diverse 2-fluoroalkylbenzothiazoles by reacting various radical sources, including perfluoroalkyl iodide (ICnF2n+1, n = 3–8, 10), ICF(CF3)2, ICF2COOEt, ICF2CF2Cl, or ICF2CF2Br, tetramethylethane-1,2-diamine (TMEDA), 2-isocyanoaryl thioethers in tetrahydrofuran under nitrogen atmosphere blue-light irradiation conditions. Furthermore, this one-pot protocol could well be expanded 2-fluoroalkylbenzoselenazoles starting from (2-isocyanophenyl)(methyl)selane, iodides 3–8) ICF2COOEt TMEDA.

Язык: Английский

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The concept of dual roles design in clean organic preparation

Chinese Chemical Letters, Год журнала: 2019, Номер 30(12), С. 2132 - 2138

Опубликована: Сен. 19, 2019

Язык: Английский

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Transition-metal-free decarboxylative C3-difluoroarylmethylation of quinoxalin-2(1H)-ones with α,α-difluoroarylacetic acids

Organic Chemistry Frontiers, Год журнала: 2019, Номер 6(8), С. 1173 - 1182

Опубликована: Янв. 1, 2019

A facile and efficient transition-metal-free decarboxylative radical coupling reaction of α,α-difluoroarylacetic acids with quinoxalin-2(1H)-ones has been developed under mild conditions.

Язык: Английский

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Metal–Ligand Cooperative Approach To Achieve Dehydrogenative Functionalization of Alcohols to Quinolines and Quinazolin-4(3H)-ones under Mild Aerobic Conditions

The Journal of Organic Chemistry, Год журнала: 2019, Номер 84(16), С. 10160 - 10171

Опубликована: Июль 22, 2019

A simple metal–ligand cooperative approach for the dehydrogenative functionalization of alcohols to various substituted quinolines and quinazolin-4(3H)-ones under relatively mild reaction conditions (≤90 °C) is reported. Simple easy-to-prepare air-stable Cu(II) complexes featuring redox-active azo-aromatic scaffolds, 2-arylazo-(1,10-phenanthroline) (L1,2), are used as catalyst. wide variety were synthesized in moderate good isolated yields via coupling reactions inexpensive easily available starting materials aerobic conditions. few control experiments deuterium labeling studies carried out understand mechanism reactions, which indicate that both copper coordinated ligand participate a manner during catalytic cycle.

Язык: Английский

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Metal‐Free Visible‐Light Promoted Radical Cyclization to Access Perfluoroalkyl‐Substituted Benzimidazo[2,1‐a]isoquinolin‐6(5H)‐ones and Indolo[2,1‐a]isoquinolin‐6(5H)‐ones

Advanced Synthesis & Catalysis, Год журнала: 2019, Номер 361(22), С. 5176 - 5181

Опубликована: Сен. 26, 2019

Abstract A metal‐free visible‐light‐induced cyclization procedure was developed for the rapid synthesis of perfluoroalkyl‐substituted benzimidazo[2,1‐ a ]isoquinolin‐6(5 H )‐ones and indolo[2,1‐ under mild reaction conditions. In this procedure, formation electron‐donor‐acceptor (EDA) complex is critical visible‐light promoted process to avoid utilization external photocatalysts. magnified image

Язык: Английский

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Recent Advances in Silver‐Mediated Radical Difunctionalization of Alkenes

ChemCatChem, Год журнала: 2020, Номер 12(21), С. 5312 - 5329

Опубликована: Июль 11, 2020

Abstract Radical‐initiated difunctionalization of alkenes is one the most important methods in organic synthesis and medicinal chemistry, which can be applied to synthesize value complex compounds as well structural motifs that found bioactive natural products pharmaceuticals. In recent years, impressive progress have been made this area with ideal silver catalysis. Here, we summarize advances silver‐mediated radical for formation diverse bonds, including 1) two‐component reactions enabled by an intramolecular cyclization process toward various cyclic 2) three‐component leading linear compounds. These alkene transformations are general initiated different radicals, such carbon‐, oxygen‐, sulfur‐, phosphinyl‐, halogen‐center followed terminated nucleophiles form two new bonds a single reaction.

Язык: Английский

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Recent applications of radical cascade reaction in the synthesis of functionalized 1-indenones

Chinese Chemical Letters, Год журнала: 2019, Номер 30(7), С. 1361 - 1368

Опубликована: Март 22, 2019

Язык: Английский

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