Sulfur-Promoted Access to 3-Arylquinoxalin-2-ones by Oxidative Coupling of o-Phenylenediamines with Arylacetates DOI

Le Anh Nguyen,

Thi Yen Nhi Tran, Quoc Anh Ngo

и другие.

Organic Letters, Год журнала: 2024, Номер 26(29), С. 6098 - 6102

Опубликована: Июль 15, 2024

We disclose the synthesis of 3-arylquinoxalin-2-ones from o-phenylenediamines and readily available arylacetates. The method harnesses selective oxidative property elemental sulfur in presence amine base catalyst DMSO. reactions are operationally simple tolerate a wide range functional groups.

Язык: Английский

Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones DOI

Jia-Cheng Hou,

Jun Jiang,

Yan-Cui Wen

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6117 - 6125

Опубликована: Апрель 24, 2024

The first paired electrolysis-enabled arylation of quinoxalin-2(1H)-ones was achieved using cyanoarenes as the reagents. A variety 3-arylquinoxalin-2(1H)-ones with various important functional groups were obtained in moderate to good yields under metal- and chemical oxidant-free conditions. With a pair reductive oxidative processes occurring among substrates reaction intermediates, power consumption can be dramatically reduced.

Язык: Английский

Процитировано

22

(Indol-3-yl)(DMIX)Iodonium Salts: Novel Electrophilic Indole Reagents DOI
Dmitry I. Bugaenko,

Nikolai A. Malashchenko,

Sergei O. Kopytov

и другие.

Organic Letters, Год журнала: 2024, Номер 26(15), С. 3189 - 3194

Опубликована: Апрель 8, 2024

A new umpolung approach to the C3–H functionalization of indoles with diverse nucleophiles based on intermediate formation I(III) reagents is described. The 3,5-dimethylisoxazol-4-yl auxiliary allows for selective indole transfer under catalyst-free conditions, which was impossible using previously reported reagents. Combining mildness transition-metal-free conditions and high reactivity hypervalent iodine reagents, this protocol tolerates various functional groups provides access that are difficult prepare conventionally.

Язык: Английский

Процитировано

9

Transition Metal and Photocatalyst Free Arylation via Photoexcitable Electron Donor Acceptor Complexes:Mediation and Catalysis DOI
Alexey A. Volkov, Dmitry I. Bugaenko, Alexander V. Karchava

и другие.

ChemCatChem, Год журнала: 2024, Номер 16(11)

Опубликована: Янв. 15, 2024

Abstract Visible‐light‐activated organic reactions unlock novel avenues for complex molecular transformations, impossible under standard “thermal” conditions, which makes them powerful tools in the arsenal of synthetic chemistry. However, transition metal‐based or photoredox catalysts are often used to ensure productive absorption visible light, might be not desirable medicinal chemistry and industry due toxicity, low sustainability, high cost most photocatalysts. A more environmentally economically benign approach is based on formation transient electron donor‐acceptor (EDA) complexes between two reagents a reagent an additive, that readily absorb acting as internal photosensitizers. Within EDA complex‐based arylation strategies, chemical transformations mediated by noncovalent interaction molecules, namely electron‐poor aryl halides their equivalents electron‐rich nucleophilic additives. Moreover, besides stoichiometric organocatalysis can achieved certain cases through regeneration donor molecules course reaction. Photoexcitation induces single transfer (SET) process generate radical species step. This Review will focus state‐of‐the‐art strategies utilizing halides, aryldiazonium, diaryliodonium, arylsulfonium arylphosphonium salts reactants, published mainly last five years.

Язык: Английский

Процитировано

7

Visible Light-Induced Electron–Donor–Acceptor-Mediated C-3 Coupling of Quinoxalin-2(1H)-ones with Unactivated Aryl Iodides DOI
Nihal Singh, Anoop Sharma, Jitender Singh

и другие.

Organic Letters, Год журнала: 2024, Номер 26(30), С. 6471 - 6476

Опубликована: Июль 23, 2024

Visible light-induced C-3 arylation of quinoxalin-2(1

Язык: Английский

Процитировано

6

Synthesis of Nonclassical Heteroaryl C-Glycosides via Decarboxylative C–H Glycosylation DOI
Cuimei Zhang,

Dongqin He,

Zhaohui Ma

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10112 - 10126

Опубликована: Июль 3, 2024

A photoredox-promoted decarboxylative C-H glycosylation for the synthesis of nonclassical heteroaryl C-glycosides is reported. This methodology characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. Moreover, operational procedure simple, gram-scale highlights practical applicability this protocol.

Язык: Английский

Процитировано

5

Visible‐light Induced C‐3 Carbamoylation of Quinoxalinones Assisted by EDA Complex DOI

Aznur Azim,

Tanumoy Mandal,

Vidhul Vasudevan

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Июнь 13, 2024

Abstract A visible‐light‐promoted strategy for the decarboxylative C‐3 carbamoylation of quinoxalinone scaffolds is developed. This approach initiates through formation an EDA complex between oxamic acid and quinoxalinone. Successive SET construct C−C bond. method utilizes aerial oxygen as green oxidant eradicates process from use external photocatalysts transition metals. Detailed synthetic photophysical studies enlighten reaction pathway.

Язык: Английский

Процитировано

4

Synthesis of Diaryl Ethers via Hypervalent Iodine-Mediated C–H Functionalization DOI

Chenghu Hu,

Qi Jia,

Wenjing Bao

и другие.

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7864 - 7868

Опубликована: Сен. 9, 2024

A hypervalent iodine-reagent-based C-H functionalization strategy was utilized to synthesize diaryl ethers. This method directly transforms various arenes into their corresponding diaryliodonium salts, followed by a C-O coupling reaction produce structurally diverse The efficacy of this approach in the late-stage structural modifications complex molecules demonstrated.

Язык: Английский

Процитировано

3

Photoinduced Metal‐/Additive‐Free Difluoromethylation of N‐Heteroaromatics DOI Open Access
Congjun Zhu, Yangyang Shen, Tao Guo

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 16, 2025

Comprehensive Summary Herein, we report a photo‐induced, metal‐/additive‐free protocol for the difluoromethylation of N ‐heteroaromatics with [bis(difluoroacetoxy)iodo]benzene as reagent. The affords difluoromethylated in moderate to good yield (up 91%). transformation is compatible wide range substrates and has tolerance towards various functional groups. Moreover, synthetic value this method further demonstrated by applications gram‐scale synthesis late‐stage functionalization biologically important molecules.

Язык: Английский

Процитировано

0

Photoinduced Vicinal Difunctionalization of Diaryliodonium Salts To Access Bis(tetraphenylphosphonium) Salts DOI
Yu Wang, Limin Wang, Jianwei Han

и другие.

Organic Letters, Год журнала: 2025, Номер 27(4), С. 1012 - 1017

Опубликована: Янв. 21, 2025

Vicinal bis(tetraarylphosphonium) salts have scarcely been reported in the literature. In this study, we demonstrate that visible-light-induced difunctionalization of ortho-trifluoromethylsulfonylated diaryliodonium conveniently furnishes bis(phosphonium) without additional catalysts or photoinitiators. The methodology establishes a practical platform for preparation using readily available tertiary phosphines. are anticipated to garner great deal interest catalytic and medicinal chemistry.

Язык: Английский

Процитировано

0

Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations DOI Creative Commons
Toshifumi Dohi, Elghareeb E. Elboray, Kotaro Kikushima

и другие.

Chemical Reviews, Год журнала: 2025, Номер unknown

Опубликована: Март 7, 2025

Constructing chemical bonds under green sustainable conditions has drawn attention from environmental and economic perspectives. The dissociation of (hetero)aryl-halide is a crucial step most arylations affording (hetero)arene derivatives. Herein, we summarize the (hetero)aryl halides activation enabling direct (hetero)arylation trapping reagents construction highly functionalized (hetero)arenes benign conditions. strategies for aryl iodides are classified into (a) hypervalent iodoarene followed by functionalization thermal/photochemical conditions, (b) aryl-I bond in presence bases with/without organic catalysts promoters, (c) photoinduced presence/absence organophotocatalysts, (d) electrochemical direct/indirect electrolysis mediated organocatalysts mediators acting as electron shuttles, (e) electrophotochemical redox-active organocatalysts. These modes result exhibiting diverse reactivity formal cations/radicals/anions aryne precursors. coupling these reactive intermediates with leads to facile selective formation C-C C-heteroatom bonds. ecofriendly, inexpensive, functional group-tolerant offer alternatives transition metal-based catalysis.

Язык: Английский

Процитировано

0