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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Silver-catalyzed decarboxylative radical cascade cyclization toward benzimidazo[2,1-a]isoquinolin-6(5H)-ones

Chemical Communications, Год журнала: 2019, Номер 55(19), С. 2861 - 2864

Опубликована: Янв. 1, 2019

A simple and efficient decarboxylative radical addition/cyclization strategy was developed, by which a wide range of benzimidazo[2,1-a]isoquinoline-6(5H)-ones were prepared in one-pot via reaction functionalized 2-arylbenzoimidazoles carboxylic acids the presence K2S2O8/AgNO3 under mild conditions.

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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Photoredox catalysis harvesting multiple photon or electrochemical energies

Beilstein Journal of Organic Chemistry, Год журнала: 2023, Номер 19, С. 1055 - 1145

Опубликована: Июль 28, 2023

Photoredox catalysis (PRC) is a cutting-edge frontier for single electron-transfer (SET) reactions, enabling the generation of reactive intermediates both oxidative and reductive processes via photon activation catalyst. Although this represents significant step towards chemoselective and, more generally, sustainable chemistry, its efficacy limited by energy visible light photons. Nowadays, excellent alternative conditions are available to overcome these limitations, harvesting two different but correlated concepts: use multi-photon such as consecutive photoinduced electron transfer (conPET) combination photo- electrochemistry in synthetic photoelectrochemistry (PEC). Herein, we review most recent contributions fields activations organic functional groups. New opportunities chemists captured, selective reactions employing super-oxidants super-reductants engage unactivated chemical feedstocks, scalability up gram scales continuous flow. This provides comparisons between techniques (multi-photon photoredox PEC) help reader fully understand their similarities, differences potential applications therefore choose which method appropriate given reaction, scale purpose project.

Язык: Английский

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Catalytic and Base‐free Suzuki‐type α‐Arylation of Cyclic 1,3‐Dicarbonyls via a Cyclic Iodonium Ylide Strategy

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(17)

Опубликована: Фев. 22, 2024

Abstract To date, it remains challenging to achieve a general and catalytic α‐arylation of cyclic 1,3‐dicarbonyls, particularly ubiquitous heteroaromatic ones. In most cases, the preparation their medically significant arylated derivatives requires multistep synthetic sequences. Herein, we introduce new, convenient strategy involving conversion 1,3‐dicarbonyls iodonium ylides ( CIY s), followed by rhodium‐catalyzed with arylboronic reagents via carbene coupling. This approach is mild, operationally simple, base‐free, biocompatible, exhibits broad substrate scope (>100 examples), especially respect various ortho ‐substituted or base‐sensitive acids. Importantly, owing excellent compatibility acids boronate esters (ArBpin, ArBneop, ArBF 3 K), this method allows late‐stage installation heterocyclic 1,3‐dicarbonyl motifs in highly complex settings. The utility transformation further demonstrated through significantly simplifying synthesis several bioactive molecules natural products.

Язык: Английский

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Oxidative Radical Relay Functionalization for the Synthesis of Benzimidazo[2,1‐a]iso‐quinolin‐6(5H)‐ones

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(10), С. 1947 - 1954

Опубликована: Фев. 18, 2020

Abstract Here, a mild and general oxidative radical relay carbocyclization reaction with 2‐arylbenzoimidazoles cyclic ethers is reported. This method provides an efficient access to wide range of structurally diverse benzimidazo[2,1‐ ]isoquinoline‐6(5 H )‐ones under metal‐free conditions. The substrate scope, good functional group tolerance, scale‐up operation this are expected promote its potential applications in biotechnology pharmacy. magnified image

Язык: Английский

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Visible-light-induced photoredox-catalyzed synthesis of benzimidazo[2,1-a]iso-quinoline-6(5H)-ones

Chinese Chemical Letters, Год журнала: 2020, Номер 32(3), С. 1229 - 1232

Опубликована: Авг. 12, 2020

Язык: Английский

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Rh(iii)-Catalyzed C–H activation/annulation of salicylaldehydes with sulfoxonium ylides for the synthesis of chromones

Organic Chemistry Frontiers, Год журнала: 2019, Номер 6(21), С. 3688 - 3692

Опубликована: Янв. 1, 2019

A rhodium(iii)-catalyzed C–H activation/annulation of salicylaldehydes with sulfoxonium ylides has been developed for the formation structurally diverse 2-substituted chromones.

Язык: Английский

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Manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles/2-arylbenzimidazoles with disubstituted phosphine oxides

Organic & Biomolecular Chemistry, Год журнала: 2020, Номер 18(25), С. 4843 - 4847

Опубликована: Янв. 1, 2020

A simple and practical method for the synthesis of phosphoryl-substituted indolo[2,1-a]isoquinolin-6(5H)-ones benzimidazo[2,1-a]isoquinolin-6(5H)-ones through manganese(iii)-promoted tandem phosphinoylation/cyclization 2-arylindoles or 2-arylbenzimidazoles with disubstituted phosphine oxides was developed. In this transformation, new C-P bond C-C were constructed simultaneously under silver-free conditions, exhibiting a broad substrate scope. It noted that not only diarylphosphine but also dialkyl arylalkyl-phosphine compatible conditions.

Язык: Английский

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