Catalytic Synthesis of Fluoroalkyl Ketones DOI

Shun‐Xi Li,

Hai‐Wu Du,

Yulong Li

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(23)

Published: Aug. 27, 2024

Abstract Fluoroalkyl ketones are a class of structural motifs which ubiquitous in bioactive molecules, and serve as synthons for diverse value‐added fluorine‐containing targets. The presence fluorine significantly alters the lipophilicity bioactivity alkyl well imposes additional challenges on synthesis fluoroalkyl ketones. Traditional methods heavily rely multiple‐step manipulations require stoichiometric reagents suffer from low efficiency. Thus, development synthesizing enabled by catalytic is highly valuable yet challenging. This Concept summarizes recent renaissance developing with substitution patterns different precursors. In addition, further efforts method also discussed.

Language: Английский

Palladium/rhodium-catalyzed four-component carbonylative difunctionalization of alkynes: Regio- and stereoselective esterification/selenylation to access β-selenyl acrylates DOI
Fengxiang Zhu, Huanan Wu, Xiao‐Feng Wu

et al.

Journal of Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 116170 - 116170

Published: April 1, 2025

Language: Английский

Citations

0
Chemoselective Synthesis of α-Halo-α,α-difluoromethyl Ketones from Trimethyl(phenylethynyl)silane DOI

Xiao‐Yan Bai,

Yuye Bai,

Ya Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4508 - 4513

Published: May 21, 2024

Here, we describe a novel strategy for chemoselective synthesis of α-halo-α,α-difluoromethyl ketones (−COCF3 and −COClCF2 motifs) from trimethyl(phenylethynyl)silane under catalyst-free mild conditions. Commercially available Selectfluor or additional NaCl as halogen reagent was employed to complete this transformation, thereby demonstrating the potential synthetic value new reaction in organic synthesis.

Language: Английский

Citations

1
Metal−Free Radical Selenothiocyanation of Terminal and Internal Alkynes DOI
Jiabin Chen, Xiaoyan Bai, Hao‐Bo Jiang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(74), P. 10196 - 10199

Published: Jan. 1, 2024

A method for inducing direct selenothiocyanation from both terminal and internal alkynes through a radical process is proposed under metal-free conditions.

Language: Английский

Citations

1
Catalytic Aldehyde–Alkyne Couplings Triggered by Ketyl Radicals DOI Creative Commons

Zhi-Xi Xing,

Shu-sheng Chen, Huan‐Ming Huang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9949 - 9954

Published: Nov. 8, 2024

A general and flexible platform for catalytic aldehyde-alkyne couplings triggered by ketyl radicals is described. This open-shell strategy necessitates only a quantity of photoredox catalyst, along with Hünig's base (DIPEA) as halogen atom transfer reagent. The reaction proceeds through sequential steps involving activation, transfer, radical addition. carbonyl-alkyne coupling exhibits wide substrate scope functional group compatibility has been successfully applied to the late-stage modification complex architectures.

Language: Английский

Citations

1
Silver-Mediated Acetoxyselenylation of Alkynes: Mild Stereoselective Access to Bifunctional Alkenes DOI

Xiao‐Yan Bai,

Jiabin Chen,

Hongxuan Du

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9811 - 9816

Published: Nov. 13, 2024

Herein, we report a AgF-mediated regio- and stereoselective acetoxyselenylation of terminal/internal alkynes from iodobenzene dicarboxylate [PhI(OCOR)2] diorganyl diselenides via multiple-site functionalization to afford β-selenyl enol esters in good yields. Alkynes derived bioactive molecules, such as l(−)-borneol, l-menthol, acyne oxalate, are also suitable for this transformation the expected compounds.

Language: Английский

Citations

1
Cu@CuFe2O4 nanoparticles catalyzed oxidative functionalization of alkynes: Access to α,α‐dichloro ketones DOI

Huahui Wang,

Sichao Wu,

Xianghua Zeng

et al.

Applied Organometallic Chemistry, Journal Year: 2024, Volume and Issue: 38(8)

Published: June 12, 2024

In this study, novel Cu@CuFe 2 O 4 nanoparticles were prepared by virtue of a simple method. By utilizing compatible system involving N‐chlorosuccinimide (NCS) as the chlorine source and magnetic (NPs) recyclable catalyst, we present practical method for directly obtaining aryl α,α ‐dichloroketones in aqueous trifluoroethanol (TFE). The catalyst was recovered reused up to five times with no significant decrease activity. current study provides foundational raw material subsequent synthesis chlorinated functional molecules, which is achieved through mild transformation arylalkynes using readily available commercial feedstocks exhibiting good tolerance various substituents on aromatic ring, including aliphatic alkyne. This heterogeneous may be used numerous industrial applications because its merits, such considerable recyclability, low requirement loading, cost‐effectiveness, ease handling.

Language: Английский

Citations

0
Late-Stage C-H Trifluoroacetylation of Quinoxaline-2(1H)-ones Using Masked Trifluoroacyl Reagents DOI
Yawei Shen, Li Yuan, Xia Wang

et al.

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

Published: Dec. 30, 2024

A strategy for trifluoroacetylation of quinoxaline-2(1 H )-ones has been investigated.

Language: Английский

Citations

0
Catalytic Synthesis of Fluoroalkyl Ketones DOI

Shun‐Xi Li,

Hai‐Wu Du,

Yulong Li

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(23)

Published: Aug. 27, 2024

Abstract Fluoroalkyl ketones are a class of structural motifs which ubiquitous in bioactive molecules, and serve as synthons for diverse value‐added fluorine‐containing targets. The presence fluorine significantly alters the lipophilicity bioactivity alkyl well imposes additional challenges on synthesis fluoroalkyl ketones. Traditional methods heavily rely multiple‐step manipulations require stoichiometric reagents suffer from low efficiency. Thus, development synthesizing enabled by catalytic is highly valuable yet challenging. This Concept summarizes recent renaissance developing with substitution patterns different precursors. In addition, further efforts method also discussed.

Language: Английский

Citations

0