Synthesis of 1,4-oxathiins via [3+3] annulation of pyridinium 1,4-zwitterionic thiolates with iodonium ylides DOI Creative Commons

Zhibin Niu,

Chao Pi, Yangjie Wu

и другие.

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

Опубликована: Июль 1, 2024

A straightforward and valuable approach for the synthesis of 1,4-oxathiins has been developed via [3 ​+ ​3] annulation pyridinium 1,4-zwitterionic thiolates with iodonium ylides. C–S C–O bonds were formed in one pot manner this transformation, which features readily available substrates, excellent tolerance functional groups mild reaction conditions. It would be great value construction biological pharmacological activity.

Язык: Английский

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents DOI Creative Commons
Akira Yoshimura, Viktor V. Zhdankin

Chemical Reviews, Год журнала: 2024, Номер unknown

Опубликована: Сен. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Язык: Английский

Процитировано

34

Generation and Application of Aryl Radicals Under Photoinduced Conditions DOI
Anupam Das, K. R. Justin Thomas

Chemistry - A European Journal, Год журнала: 2024, Номер 30(31)

Опубликована: Март 28, 2024

Abstract Photoinduced aryl radical generation is a powerful strategy in organic synthesis that facilitates the formation of diverse carbon‐carbon and carbon‐heteroatom bonds. The synthetic applications photoinduced complex compounds, including natural products, physiologically significant molecules, functional materials, have received immense attention. An overview current developments production methods their uses given this article. A generalized idea how to choose reagents approach for radicals described, along with techniques associated mechanistic insights. Overall, article offers critical assessment results as well selection reaction parameters specific context cascades, cross‐coupling reactions, functionalization, selective C−H functionalization substrates.

Язык: Английский

Процитировано

16

Visible-Light Induced Organophotocatalysis for the Synthesis of Difluoroethylated Benzoxazines DOI Open Access
Xiang Chen, Wen‐Tao Ouyang, Xiao Li

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(12), С. 4213 - 4213

Опубликована: Янв. 1, 2023

Benzoxazines are important motif in pharmaceuticals and functional molecules.A visible-light induced photocatalytic strategy for the synthesis of difluoroethyl benzoxazines with organo-photocatalyst was developed.In present protocol, a series olefinic amides can be transferred to difluoroethylated via oxydifluoromethylation CF2HSO2Na as difluoromethylating reagent, which is easily operated good group tolerant.

Язык: Английский

Процитировано

22

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

Visible Light‐Induced Arylation/Alkylation/Phosphorylation of Isocyanides viaEDA Complex Activation DOI Open Access

Shichao Yang,

Xiangwen Tan,

Dan Liu

и другие.

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

Опубликована: Март 20, 2025

Comprehensive Summary Herein, it is reported that the aryl radicals derived from thianthrenium salts are used as coupling partner in arylation reactions of isocyanides, simultaneously initiators for formation alkyl and phosphoryl ethers diarylphosphine oxides. This cascade cyclization reaction leads to diverse arylated, alkylated phosphorylated heteroaromatic compounds. Notably, this transformation can be achieved without aid metals or photocatalysts, exhibiting a wide substrate applicability operational simplicity. Mechanistic studies suggest involvement radical processes electron donor‐acceptor (EDA) complexes transformation.

Язык: Английский

Процитировано

0

Visible-light-induced radical cascade cyclization of 2-isocyanobiaryls via 1,5-hydrogen atom transfer (1,5-HAT) DOI

Yafei Zhu,

Penghua Zhang,

Xingqin Tian

и другие.

Organic Chemistry Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

We reported the first example of visible-light-induced radical cascade cyclization 2-isocyanobiaryls via 1,5-HAT, which is characterized by broad substrate scope, excellent functional group compatibility and no requirement any metals base.

Язык: Английский

Процитировано

0

Recent Advancement of 1,2,3,5‐Tetrakis(Carbazol‐9‐yl)‐4,6‐Dicyanobenzene (4‐CzIPN) in Photocatalyzed Synthesis of Heterocyclic Compounds DOI

Km Garima,

Vishal Srivastava, Praveen P. Singh

и другие.

ChemistrySelect, Год журнала: 2025, Номер 10(17)

Опубликована: Май 1, 2025

Abstract 4‐CzIPN is a traditional electron donor and acceptor fluorophore that uses carbazolyl as an donating dicyanobenzene withdrawing source. Its broad redox potential, high chemical resistance wide applicability makes it unique metal‐free photocatalyst. This study summarizes the recent development of photoredox catalyst for variety heterocyclic construction over last four years (2021‐2024).

Язык: Английский

Процитировано

0

Recent Advancements in Synthesis of Phenanthridines via 2‐Isocyanobiphenyls DOI Open Access
Ashutosh Dey, Vikash Kumar, Rana Chatterjee

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(11)

Опубликована: Сен. 22, 2023

Abstract Phenanthridines are a privileged heterocyclic compound that exists in many natural products and has been known to exhibit variety of pharmacological properties. In the last few decades, an incredible development taken place synthesise this scaffold. regard, 2‐isocyanobiphenyl become one most exploited substrates allow direct formation phenanthridine derivatives under various novel conventional methods. The present review provides overview synthetic approaches for preparation phenanthridine, their form 2‐isocyanobiphenyls′′.

Язык: Английский

Процитировано

8

Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh3 Catalysis DOI

Jia‐Li Sui,

Xin‐Qian Liu,

Shun‐Dan Li

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 10, 2024

Comprehensive Summary A visible‐light‐induced decarboxylative radical cascade cyclization reaction between N ‐(2‐cyanoaryl)‐acrylamides and alkyl ‐(acyloxy)phthalimide (NHPI esters) for the construction of phenanthridine derivatives has been developed. This approach utilizes lithium iodide (LiI) triphenylphosphine (PPh 3 ) as redox catalysts is produced through photoactivation electron donor‐acceptor (EDA) complex. series primary, secondary, tertiary alkyl‐substituted phenanthridines are prepared in up to 82% yield without transition‐metal catalysts, chemical oxidants, or metal‐/organic dye‐based photocatalysts.

Язык: Английский

Процитировано

2

Visible-Light-Mediated Annulation/Thiolation of 2-Isocyanobiaryls with Disulfides to Organoylthiophenanthridines Derivatives DOI
Hongyu Wu, Zhong Cao, Shiqi Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 17322 - 17329

Опубликована: Дек. 4, 2023

A visible-light-induced annulation/thiolation of 2-isocyanobiaryls with dialkyl(aryl)disulfides has been established, delivering a sustainable and atom-economic route to 6-organoylthiophenanthridines wild functional group tolerance good excellent yields under oxidant-, base-, transition-metal-free conditions.

Язык: Английский

Процитировано

5