Cobalt-Catalyzed Oxyalkylation Reaction of Styrenes: Rapid Access to α-Alkyl Substituted Acetophenone Derivatives DOI Open Access
Peng Zhou, Weiming Zhu, Jiantao Zhang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(11), P. 3939 - 3939

Published: Jan. 1, 2023

Alkyl aryl ketones are a class of valuable compounds in chemistry and biology, which widely used the pharmaceutical, spice, dye, pesticide, functional materials, organic synthesis industries.A cobalt-catalyzed oxyalkylation reaction olefin with tert-butyl hydroperoxide (TBHP) cyclic ethers was developed.Various substrates electron-withdrawing or electron-donating groups were tolerated this protocol to provide α-alkyl substituted acetophenones moderate yields.The present features broad substrate scope, flexibility, allowing rapid assembly series value-added acetophenone derivatives under mild conditions good efficacy.

Language: Английский

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions DOI

Liguo Lu,

Dayun Huang, Zefeng Wang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(14), P. 2310 - 2331

Published: June 24, 2023

Abstract Alkenes are valuable feedstocks in organic synthesis. Selenium or sulfur‐containing coumpounds with a neighboring functional group can be easily prepared by direct difunctionalization of alkenes via three‐component reactions. It will reduce the number steps and waste generation, form complicated molecules from simple starting materials. Herein, recent developments (2013–2022) have been summarized two categories: (1) selenylation seleniranium intermediates Se‐centered radicals; (2) thiolation more diverse mechanisms products Reactions electron‐rich arenes, alcohols, water, acids, NaN 3 , amines, KSCN, sulfamides, TMSNCS, TMSN Et N ⋅ 3HF, SOCl 2 HCl, NFSI, t BuONO, pyridinium salts, BuOOH, ArN BF 4 CO CO, O CF SO Cl, R P(O)−H, (RO) P(O)SH, P(O)OH et al discussed. We hope this review do help for future research area.

Language: Английский

Citations

15

Design of a Bilateral Disulfurating Reagent for Unsymmetrical Polysulfidation DOI

Qingqiang Tian,

Yahui Li

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(25)

Published: April 22, 2023

In this study, we designed a bilateral disulfurating reagent via S-S motif "snip and stitch" processes, allowing diverse functional groups to be bridged bonds. The is readily synthesized in high yield using one-step reaction from easily available starting materials air-stable. With reagent, electrophiles including inactivated alkyl Cl/Br/I/OMs benzyl chloride were sequentially installed on either side of the motif. Natural products, agrochemicals, pharmaceuticals can successively cross-linked with Notably, used cyclic disulfide synthesis. At last, some desired products work showed good antibacterial activities, which could employed as novel candidates control plant pathogenic bacteria.

Language: Английский

Citations

13

From S-Fluoroalkylation to Fluoroalkylation–Thiolation: Difunctionalization of Alkenes with Fluoroalkyl Phenyl Sulfones and Thiophenols Enabled by Photoredox Copper Catalysis DOI
Xiao Lin, Zhiqiang Wei, Chuanfa Ni

et al.

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

Published: Feb. 17, 2025

Molecules containing fluoroalkyl and arylthio groups play a pivotal role in pharmaceutical agrochemical development. The simultaneous introduction of these functional through the 1,2-difunctionalization alkenes is an efficient strategy. Fluoroalkyl phenyl sulfones serve as accessible radical precursors; however, their tendency to interact with thiophenol via electron donor–acceptor interaction mechanism can impede desired transformation. Through meticulous selection solvent base, we successfully utilized copper catalysis facilitate alkene-involved three-component reaction. Our work unveils photoredox copper-catalyzed fluoroalkylation–thiolation using various (such perfluoroethyl, tetrafluoroethyl, trifluoromethyl, difluoromethyl, difluoroalkyl, difluorobenzyl). efficacy this approach exemplified by synthesis Kengreal derivatives.

Language: Английский

Citations

0

Iron-catalysed reductive coupling for the synthesis of polyfluorinated compounds DOI
Yu‐Qiu Guan,

Tian‐Zhang Wang,

Jia-Fan Qiao

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(100), P. 13915 - 13918

Published: Jan. 1, 2022

Herein we reported the use of Earth-abundant iron as catalytic metal in presence Mn to induce difluorobromoacetates form carbon radicals, which reacted with trifluoromethyl olefins followed by β-F elimination generate corresponding gem-difluoroolefins. The cross-electrophile coupling displayed excellent functional group tolerance and broad substrate scope under mild reductive conditions, affording a large number polyfluorinated compounds, could be further transformed other valuable molecules.

Language: Английский

Citations

16

Highly Regioselective Synthesis of N‐β‐trifluoromethyl 2‐pyridones via anti‐Markovnikov Hydroamination of α‐(trifluoromethyl)styrenes with 2‐pyridones DOI Open Access
Yi Zhang,

Zhudi Sun,

Jingjing He

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(10)

Published: April 8, 2023

Abstract A novel and facile method for the synthesis of N ‐β‐CF 3 ‐substituted 2‐pyridones via hydroamination α‐(trifluoromethyl)styrenes with was described. The reaction proceeded smoothly at room temperature, affording a variety ‐(β‐trifluoromethyl‐β‐arylethyl)pyridin‐2(1 H )‐ones in moderate to good yields excellent ‐regioselectivity.

Language: Английский

Citations

10

Current State of Microflow Trifluoromethylation Reactions DOI
Yuji Sumii, Norio Shibata

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(9)

Published: June 12, 2023

Abstract The trifluoromethyl group is a powerful structural motif in drugs and polymers; thus, developing trifluoromethylation reactions an important area of research organic chemistry. Over the past few decades, significant progress has been made new methods for molecules, ranging from nucleophilic electrophilic approaches to transition‐metal catalysis, photocatalysis, electrolytic reactions. While these were initially developed batch systems, more recent microflow versions are highly attractive industrial applications owing their scalability, safety, time efficiency. In this review, we discuss current state trifluoromethylation. Approaches based on different reagents described, including continuous flow, flow photochemical, microfluidic electrochemical reactions, large‐scale

Language: Английский

Citations

6

PPh3‐Mediated Nucleophilic Sulfonation of Sulfonyl Chlorides with Arynes: Access to Manifold Aryl Sulfones DOI

Hui‐Qi Yue,

Qiwei Li, Dawei Shi

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(39)

Published: Aug. 19, 2023

Abstract Sulfonyl chlorides are a class of cheap and readily available basic chemicals, which have routinely served as electrophilic reagents in their chemical transformations. Herein, we disclose novel PPh 3 ‐mediated nucleophilic sulfonation method sulfonyl with arynes. Different from the classical P(III)‐mediated reductive deoxygenation reaction chlorides, valence state sulfur atom has not been changed. This protocol exhibits broad functional group tolerance provides direct approach to variety aryl alkyl sulfones.

Language: Английский

Citations

4

Facile synthesis of β‐trifluoromethyl thioethers via DBN‐catalyzed hydrothiolation of a‐trifluoromethyl styrenes with thiols DOI

Yupian Deng,

Jia‐Qi Huang,

Yuhao Qian

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(20)

Published: July 23, 2024

Abstract A very simple and atom‐economical method for the synthesis of vicinal trifluoromethyl thioethers via DBN‐catalyzed hydrothiolation α‐(trifluoromethyl)styrenes with thiols was reported. The reaction proceeded smoothly under mild conditions provided β‐CF 3 ‐thioethers in moderate to good yields an anti‐Markovnikov manner. Furthermore, this features several remarkable advantages, such as use a catalytic amount DBN, broad substrate scope, excellent functional group compatibility, easy scalability.

Language: Английский

Citations

1

Enhancing Efficiency and Sustainability: Unleashing the Potential of Continuous Flow in Multicomponent Reactions DOI
Marcelo H. R. Carvalho, Pedro P. de Castro, Kléber T. de Oliveira

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 11, 2024

The integration of multicomponent reactions (MCRs), which offer a rapid and efficient approach to synthesize complex molecular scaffolds, with continuous flow platforms is an increasingly recognized strategy in green synthesis. This association enables precise control over reaction parameters, including improved kinetics selectivity, reduced times, enhanced yields scalabilities, while aligning sustainable chemistry principles through resource utilization, minimized waste, environmental impact. review presents critical analysis recent studies covering the MCR-continuous association, focus on achieving greener more synthesis practices.

Language: Английский

Citations

1

Design, Synthesis and Application of a Robust d3‐Methylthiolating Reagent DOI
Yanyang Zhang,

Yishuo Ren,

Jian Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(22), P. 3045 - 3049

Published: July 15, 2023

Comprehensive Summary A deuterated methylthiolating reagent with a broad spectrum, designated as DMTP, has been ingeniously formulated. This new can be produced high efficiency through the simple combination of commercially available methyl 3‐thiopropanoate and CD 3 I. novel SCD exhibits excellent reactivity electrophiles such alkyl iodides, benzyl chlorides, aryl halides (I, Br) triflates, resulting in levels deuterium content (99% D). Representative methylthiolated biomolecules, Sulfoxaflor, have synthesized for use pharmaceutical discovery development.

Language: Английский

Citations

2