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

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: July 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.

Language: Английский

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

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 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.

Language: Английский

Citations

28

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

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(31)

Published: March 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.

Language: Английский

Citations

13

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

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(12), P. 4213 - 4213

Published: Jan. 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.

Language: Английский

Citations

20

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

et al.

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: March 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.

Language: Английский

Citations

0

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

Shichao Yang,

Xiangwen Tan,

Dan Liu

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 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.

Language: Английский

Citations

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

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 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.

Language: Английский

Citations

0

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

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(11)

Published: Sept. 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′′.

Language: Английский

Citations

8

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

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 17322 - 17329

Published: Dec. 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.

Language: Английский

Citations

4

Visible-Light-Driven α-C(sp3)–H Bond Functionalization of Glycine Derivatives DOI Open Access

Yao Tian,

Xiubin Bu,

Yuanrui Chen

et al.

Catalysts, Journal Year: 2023, Volume and Issue: 13(12), P. 1502 - 1502

Published: Dec. 8, 2023

The glycine motif is widely prevalent in bioactive peptides. Thus, the direct and precise modification of derivatives has attracted significant attention over past few decades. Among various protocols for derivatives, visible-light-driven α-C(sp3)–H bond functionalization emerged as a powerful tool to achieve this objective, owing its merits atom economy, selectivity, reaction simplicity, sustainability. This review summarizes recent advancements derivatives. contents are organized based on photocatalysts employed modes process. mechanism, challenges encountered, future trends also discussed, enabling readers understand current developmental status field.

Language: Английский

Citations

4

Visible-Light-Induced Cascade Azidation/Cyclization of Activated Alkenes to Synthesize Azidated Indolo[2,1-a]isoquinolines DOI
Yucai Tang, Yu‐Peng He,

Biyu Yang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(7), P. 2286 - 2286

Published: Jan. 1, 2024

Language: Английский

Citations

1