The Electrochemical trans-Chloroformyloxylation of Unactivated Alkenes DOI

Jona Queder,

Gerhard Hilt

Synlett, Journal Year: 2024, Volume and Issue: 35(16), P. 1906 - 1908

Published: March 20, 2024

Abstract An attempted aryl selenium-catalyzed formation of cis-chlorohydrins from alkenes was unsuccessful but led to an electrochemical investigation for the trans-selective chloroformyloxylation cyclic and acyclic in moderate good yields. Interestingly, when 1,1-disubstituted were used, corresponding vinyl chloride derivatives obtained, application 1-phenylcyclohex-1-ene allyl derivative.

Language: Английский

Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation DOI
Jianchao Liu, Jie‐Ping Wan, Yunyun Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 597 - 630

Published: Nov. 23, 2023

This review highlights the recent progress in electrochemical difunctionalization of alkenes and alkynes involving C–S/Se bond formation to access organochalcogen frameworks.

Language: Английский

Citations

30

Regio- and stereoselective electrochemical selenoalkylation of alkynes with 1,3-dicarbonyl compounds and diselenides DOI

Zhong‐Wei Hou,

Laiqiang Li, Lei Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(10), P. 2815 - 2820

Published: Jan. 1, 2022

A regio- and stereoselective electrochemical approach for the selenoalkylation of alkynes with 1,3-dicarbonyl compounds diselenides has been developed.

Language: Английский

Citations

37

Recent advances in the synthesis of 2,3-fused quinazolinones DOI

Wang Wang,

Pei‐Sen Zou,

Li Pang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(32), P. 6293 - 6313

Published: Jan. 1, 2022

As one of the most important structural units in pharmaceuticals and medicinal chemistry, quinazolinone its derivatives exhibit a wide range biological pharmacological activities, including anti-inflammatory, antitubercular, antiviral, anticancer etc. In particular, 2,3-fused quinazolinones have attracted much attention because rings fused to 2,3-positions improve their rigidity planarity. Their synthetic strategies made great advances recent years. Therefore, this review focuses on novel for synthesis from 2017 2022, such as difunctionalization alkenes, ring-opening easily available small rings, dehydrogenative cross-coupling reactions, transition-metal catalyzed cyclizations, cycloadditions, other cascade reactions.

Language: Английский

Citations

30

Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization DOI
Chang‐Sheng Wang,

Yuan Xu,

Yiliang Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4972 - 5027

Published: Jan. 1, 2023

This review comprehensively summarizes the dichalcogenative functionalization of unsaturated compounds over past decade. The scopes, limitations and detailed reaction mechanisms are also discussed.

Language: Английский

Citations

20

Photocatalytic C−C Cleavage of Methylenecyclobutanes for γ,δ‐Unsaturated Aldehydes by Strain Release DOI Creative Commons
Yan Zhang,

Chunhang Zhao,

Chanchan Ma

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(22)

Published: March 6, 2023

Radical additions onto olefins have surfaced as an increasingly powerful strategy for the synthesis of difunctionalized scaffolds. However, despite major advances, known approaches continue to be largely limited two manifolds, namely 1,2-difunctionalization alkenes and remote difunctionalization via hydrogen atom transfer (HAT). Herein, we describe a mechanistically distinct approach by photoinduced carbon-carbon (C-C) activation/ring-opening access γ,δ-unsaturated aldehydes from methylenecyclobutanols sulfonyl chlorides strain release. Remarkably, motif on products was easily removed another photocatalytic process, which enabled concise assembly natural product alatanone A. The synthetic utility our reflected versatile functional group tolerance, ample substrate scope, scalability. photocatalysis represents conceptually alternative existing 1,4-diversifications, with double bond remaining in thus obtained products.

Language: Английский

Citations

18

Merging Copper(I) Photoredox Catalysis and Iodine(III) Chemistry for the Oxy‐monofluoromethylation of Alkenes DOI
Nagarajan Ramkumar,

Л. Баумане,

Dzintars Začs

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(12)

Published: Jan. 24, 2023

A simple process for the oxy-monofluoromethylation of alkenes is described. In combination with visible-light copper(I) photoredox catalysis, an easily accessible iodine(III) reagent containing monofluoroacetoxy ligands serves as a powerful source monofluoromethyl (CH2 F) radical, enabling step economical synthesis γ-fluoro-acetates from broad range olefinic substrates under mild conditions. Applications to late-stage diversification derived complex molecules, amino acids and fluoromethylated heterocycles are also demonstrated.

Language: Английский

Citations

17

Electrochemical conversion of organic compounds and inorganic small molecules DOI

Wei-Mei Zeng,

Youai Qiu

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(10), P. 3223 - 3246

Published: July 9, 2024

Language: Английский

Citations

7

Recent Advances in Electrochemical Synthesis of Nitriles: A Sustainable Approach DOI

Roopa Margaret Rodrigues,

Ditto Abraham Thadathil,

P. Keerthana

et al.

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(12)

Published: March 23, 2022

Abstract Nitriles unveil widespread applications in pharmaceuticals, agrochemicals, textiles, rubber, polymers, and constitute a significant intermediate several organic transformations, necessitating the design of simple environmentally benign pathways for their synthesis. Over recent years, electro‐organic reactions have found attention developing effective selective They possess advantages: high atom economy, selectivity, minimal waste production, shorter routes to multistep traditional reactions. The development novel strategies greener sustainable synthesis nitriles is therefore commendable. This review focuses on analyzing various methods used electrochemical using phase transfer catalyst, N‐oxoammonium salts mediated electrocatalysis, iodine‐mediated anodic oxidations aldoximes. In addition, trends including via C−H cyanation, domino oxidation, bio metal‐ligand cooperative been discussed.

Language: Английский

Citations

27

Electrochemical Difunctionalization of gem-Difluoroalkenes: A Metal-Free Synthesis of α-Difluoro(alkoxyl/azolated) Methylated Ethers DOI

Linzi Wen,

Naifu Zhou, Zhicheng Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(18), P. 3308 - 3313

Published: May 2, 2023

A scalable electrochemical difunctionalization of gem-difluoroalkenes to structurally versatile difluoro motifs was achieved. This methodology features reagent-free conditions, good functional group tolerance, and a relatively broad substrate scope. Meanwhile, the electrolysis protocol is easy handle, products show regio- chemoselectivity. The reaction mechanism also preliminarily studied.

Language: Английский

Citations

11

Recent Progress on the Electro-Organic Synthesis for the 1,2-Difunctionalization of Alkenes DOI
Mingming Zhang, Ting Liu,

Xue-Qiu Chen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: 23(10), P. 2323 - 2357

Published: Jan. 1, 2025

In recent years, significant achievements have been made in the field of electroorganic chemistry regarding difunctionalization alkenes. Researchers developed innovative strategies utilizing unique reactivity electrochemical processes to synthesize complex molecules with high regioselectivity and stereoselectivity. This technology is widely applied total synthesis natural products pharmaceutical industry. article reviews research progress alkenes through three different radical-mediated pathways over past five years. It includes discussions on 1,2-stereoselective non-diastereoselective reactions, rearrangements, intramolecular migrations, cyclization processes. The summary emphasizes electrode designs, reaction mechanisms, integration other emerging technologies, highlighting potential this method modern organic chemistry. Additionally, it aims address current challenges propose possible solutions, providing a promising direction for electrochemically mediated reactions

Language: Английский

Citations

0