Photoinduced EDA Complex‐initiated Synthesis of Fluoroalkylated Isoquinolinonediones DOI Open Access
Lei Huang,

Chaodong Wang,

Zhi Chen

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 6, 2024

Abstract A visible‐light‐induced radical tandem difluoroalkylation/cyclization to construct CF 2 ‐containing isoquinolinonedione skeletons with methacryloyl benzamides is developed. Broad substrate scopes are compatible metal‐, oxidant‐ and photocatalyst‐free conditions under room temperature in good‐to‐excellent yields. Mechanistic analysis revealed that the transformation initiated by photoinduced electron donor‐acceptor (EDA) complexes formation.

Language: Английский

Photoredox-Enabled Direct and Three-Component Difluoroalkylative Modification of N-Aryl Glycinates DOI
Fangyuan Yu,

Daoyi Yang,

Yuanlin Yang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 1072 - 1077

Published: Jan. 18, 2025

A Cu(I) photoredox-enabled reaction that selectively incorporates a difluoroalkyl group into N-aryl glycine derivatives has been established. Using bench-stable [Ph3PCF2H]+Br- salt, the -CF2H could be installed either directly on α-carbon of backbone or in three-component fashion using an alkene as bridge. series have evaluated, providing access to diverse unnatural amino esters and dipeptides with -CHF2 unit. The studies compatibility other perfluorinated alkyl radical precursors showed selectivity direct α-coupling is closely associated electronic property radical, while works well most cases.

Language: Английский

Citations

1

N-Phenylphenothiazine-based Hyper-cross-linked Polymers for Recyclable, Heterogeneous Photocatalysis of Organic Transformations: A Strategy to Access 6-Difluoromethyl-phenanthridines DOI

Shengjie Song,

Wenjian Wang,

Yali He

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

Herein, a N-phenylphenothiazine-based hyper-cross-linked polymer (PTH-HCP) was finely designed and constructed, which serves as metal-free heterogeneous photocatalyst for organic transformations. Characterization experiments have shown that this demonstrates outstanding stability, extensive surface area, exceptional photoelectric response properties. Moreover, PTH-HCP showed good catalytic efficiency recyclability in the photochemically driven difluoromethylation/cyclization reactions. This work provides strategy design construction of photocatalysts offers support their broad prospects synthetic applications.

Language: Английский

Citations

1

Visible‐Light‐Promoted Difluoromethylation/Cyclization of 1‐Acryloyl‐2‐cyanoindole for Construction of Difluoromethylated Pyrrolo[1,2‐a]indolediones DOI

Hongzhao Qu,

Jinwei Yuan, Zhendong Feng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1158 - 1164

Published: Jan. 10, 2024

Abstract A visible‐light‐promoted cascade difluoromethylation/cyclization reaction to access various difluoromethylated pyrrolo[1,2‐ a ]indolediones was developed using difluoromethyltriphenylphosphonium bromide salt as the difluoromethylating reagent. possible radical mechanism has been investigated and proven single electron transfer (SET) procedure.

Language: Английский

Citations

7

Visible Light-Induced Radical Cascade Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Polycyclic Imidazoles DOI Creative Commons
S.J. Lin, Yuanyuan Deng,

Hanxun Zhong

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: 9(26), P. 28129 - 28143

Published: June 19, 2024

An efficient and mild protocol for the visible light-induced radical cascade difluoromethylation/cyclization of imidazoles with unactivated alkenes using easily accessible bench-stable difluoromethyltriphenylphosphonium bromide as precursor -CF

Language: Английский

Citations

5

Introduction of Difluoromethyl through Radical Pathways DOI
Xin Li, Qiuling Song

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(31)

Published: June 5, 2024

Abstract During the past decade, radical difluoromethylation has emerged as a powerful and versatile tool for incorporation of difluoromethyl into various organic compounds. These reactions feature mild reaction conditions, very good functional group compatibilities, quite broad substrate scopes, thus having drawn much attention got rapid developments. A diverse range precursors have been developed series reactions. This review summarizes discusses advance in reactions, which are organized according to protocols generating radical.

Language: Английский

Citations

4

Photo-promoted radical cascade cyclization of 4-(allylamino)-3-cyanocoumarins: access to sulfonylated pyrido[3,2-c]coumarin derivatives DOI
Luyao Yang, Jun Ying, Hao Zheng

et al.

Green Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The first method for constructing pyrido[3,2- c ]coumarin derivatives via a radical cascade cyclization process was proposed, which can introduce active fragments.

Language: Английский

Citations

0

Diazonium Salts Induced Divergent Synthesis of α,β‐Unsaturated‐Azo‐Substituted‐Quinazolin‐2(1H)‐ones and Quinolinones via Sequential Cyclization and Skeletal Rearrangement DOI
Wenkai Huang, Peng Zhang, Xue Yang

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(14)

Published: April 1, 2025

Abstract We have successfully developed a novel synthetic route for the synthesis of α,β‐unsaturated‐azo‐substituted‐quinazolin‐2(1 H )‐one via reaction between 1,3‐diphenylurea analogues and diazonium salts, facilitated by salt‐induced intramolecular cyclization process. Notably, this exhibits remarkable tolerance toward wide range substituents, resulting in formation diverse products under mild conditions. Additionally, we discovered that rearrangement occurs alkaline conditions, leading to α,β‐unsaturated‐azo‐substituted‐quinolinone derivatives.

Language: Английский

Citations

0

Photoredox-Catalyzed Direct C(sp2)–H Difluoromethylation of Hydrazones with Difluoromethyltriphenylphosphonium Salt via Aminyl Radical/Polar Crossover DOI

Xiao‐Di Wu,

Wang Li,

Ji‐Yu Tao

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 10, 2025

This study describes an efficacious and generally applicable synthetic strategy for the incorporation of biologically physiologically prominent difluoromethyl entity into synthetically crucial hydrazone scaffolds with bench-stable easily accessible difluoromethyltriphenylphosphonium bromide. The broad substrate scope, excellent functional group compatibility, feasibility step atom economical one-pot manipulation, environmentally benign mild reaction conditions rendered this methodology efficient tool preparation pharmaceutically fluorine-containing imino compounds.

Language: Английский

Citations

0

Photoinduced Metal-Free Radical Addition/Cyclization of 2-Cyanoaryl Acrylamides to Prepare gem-Difluorinated Naphthyridinone Scaffolds DOI

Qiaoyan Wu,

Meilin Ren,

Zhike Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10831 - 10843

Published: July 11, 2024

Direct construction of

Language: Английский

Citations

1

Photo-Induced Difluoroalkylation/Cyclization of Alkyne Ketones: A Novel Strategy to Access Difluoroalkyl Thiofavones DOI

Shengjie Song,

Can Luo,

Guan Wang

et al.

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

Published: Jan. 1, 2024

A photo-induced electron donor-acceptor (EDA) complex enabled tandem reaction of alkyne ketones

Language: Английский

Citations

1