Selectfluor-triggered C–H halogenations of enaminones with copper(I) halide (CuX) for the synthesis of 3-halochromones DOI
Tian Ma,

Xiaoli Li,

Jinwei Yuan

et al.

Zeitschrift für Naturforschung B, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 3, 2024

Abstract A practical and efficient synthetic route to construct a variety of 3-halochromones has been realized using Selectfluor reagent as fluorine source, or Selectfluor-copper(I) halide combination halogen source under mild conditions. This reaction proceeds via sequence electrophilic cation addition, cyclization leading broad range in good excellent yields short period time. Additionally, the utilization commercially available cost-effective copper(I) renders this system highly practical.

Language: Английский

Photo-induced synthesis of fluoroalkylated quinolinones via an iron-catalyzed LMCT decarboxylation process DOI

Zhuoheng Song,

Guo Lin, Chao Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(16), P. 4436 - 4441

Published: Jan. 1, 2024

A general synthesis of fluoroalkylated quinolone compounds using a visible-light-induced iron catalyzed LMCT method is reported herein.

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

Visible-light-induced photocatalyst-free cascade cyclization of 3-(2-(ethynyl)phenyl)quinazolinones to sulfonated quinolino[2,1-b]quinazolinones DOI

Fan‐Lin Zeng,

Lili Wang,

Yuxin Luo

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(56), P. 7228 - 7231

Published: Jan. 1, 2024

A visible-light-induced K 2 S O 8 -promoted cascade sulfonation/cyclization reaction to afford a series of sulfonated quinolino[2,1- b ]quinazolinones has been developed under mild conditions.

Language: Английский

Citations

4

Photo-induced decarboxylative radical cascade cyclization of unactivated alkenes: access to CF- and CF2-substituted ring-fused imidazoles DOI Creative Commons
Hui-Nan Wang, Shaohui Lin, Hui Hong

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(16), P. 12739 - 12745

Published: Jan. 1, 2025

A mild and effective visible-light-induced decarboxylative radical cascade reaction of olefin-containing imidazoles α-fluorinated carboxylic acids, has been developed to afford monofluoromethylated or aryldifluoromethylated polycyclic imidazoles.

Language: Английский

Citations

0

Phototriggered Fluoroalkylation/Cyclization of Unactivated 1-Acryloyl-2-cyanoindoles: Synthesis of RCOCF2-Substituted Pyrrolo[1,2-a]indolediones DOI

Weixian Lv,

Pengyuan Yang,

Jinwei Yuan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3525 - 3537

Published: Feb. 16, 2024

A photochemical approach toward RCOCF2-substituted pyrrolo[1,2-a]indolediones was developed by the radical cascade difluoroalkylation/cyclization reaction of unactivated 1-acryloyl-2-cyanoindoles with ethyl iododifluoroacetate or iododifluoramides under visible-light irradiation. This transition-metal- and photosensitizer-free protocol afforded diverse difluoroalkylated in moderate to good yields mild conditions. Most appealingly, can proceed smoothly sunlight irradiation, which opens a new avenue pyrrolo[1,2-a]indolediones.

Language: Английский

Citations

2

Insight into C4 Selectivity in the Light‐Driven C–H Fluoroalkylation of Pyridines and Quinolines DOI

Leejae Kim,

Wooseok Lee, Sungwoo Hong

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(46)

Published: Aug. 9, 2024

Abstract Given the prevalence of pyridine motifs in FDA‐approved drugs, selective fluoroalkylation pyridines and quinolines is essential for preparing diverse bioisosteres. However, challenges are often faced with conventional Minisci reactions achieving precise regioselectivity owing to competing reaction sites limited availability fluoroalkyl radical sources. Herein, we present a light‐driven, C4‐selective azines utilizing N‐aminopyridinium salts readily available sulfinates. Our approach employs electron donor‐acceptor complexes, highly under mild conditions without an external photocatalyst. This practical method not only enables installation CF 2 H groups but also allows incorporation ‐alkyl functional entities, surpassing limitations previous methods. The versatility pathway further demonstrated through straightforward three‐component involving alkenes [1.1.1]propellane. Detailed experimental computational studies have elucidated origins regioselectivity, providing profound insights into mechanistic aspects.

Language: Английский

Citations

2

Metal-free nitro/azido cyclization of 1-acryloyl-2-cyanoindoles to access NO2/N3-featured pyrrolo[1,2-a] indolediones DOI
Huaqing Liu,

Qinqin Yan,

Yanzhao Zeng

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(32), P. 6490 - 6494

Published: Jan. 1, 2024

An H

Language: Английский

Citations

1

Visible-Light Induced Iron-Catalyzed Hydroxymethylation of N-Heterocycles DOI
Yan‐Hua Fu,

Chang Xu,

Chao Zhang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(7), P. 2265 - 2265

Published: Jan. 1, 2024

Language: Английский

Citations

1

Visible-Light-Induced Dearomative Annulation of Indoles toward Stereoselective Formation of Fused- and Spiro Indolines DOI Creative Commons
Suven Das

ACS Omega, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 13, 2024

Dearomatization approaches are attractive for their abilities to transform simple, planar arenes into complex, three-dimensional architectures. In particular, visible-light driven dearomatization strategies significant because of mild, green, and sustainable nature, enabling the fabrication new chemical bonds via an electron transfer or energy process. Indole compounds, being potentially bioactive readily accessible, can be employed efficiently as building blocks constructing diverse annulated frameworks under photocatalysis. Highly stereoselective radical cascade reactions appropriate indole systems provide complex cyclic scaffolds bearing multiple stereocenters. fact, past few years have witnessed renaissance dearomative cycloadditions indoles visible-light-induced The present review highlights recent advances (2019–mid 2024) in visible-light-driven annulation leading formation polycyclic indolines, including angularly fused spiro indolines. Most described this providing quick access desired products. Additionally, characteristic reaction mechanisms offered understand how show distinctive reactivity photocatalytic conditions.

Language: Английский

Citations

1

Visible-light-induced decarboxylative cyclization DOI
Suven Das

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 3, 2024

The present review focuses on recent progress (2020–2024) in the visible-light-driven decarboxylative cyclization of various carboxylic acid derivatives for constructing carbo-/heterocycles.

Language: Английский

Citations

1