Electrosynthesis of CF3‐Substituted Polycyclic Quinazolinones via Cascade Trifluoromethylation/Cyclization of Unactivated Alkene DOI
Lei Liu,

Wangqin Zhang,

Chao Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(7), P. 1319 - 1325

Published: Feb. 23, 2022

Abstract An atom and step economy cascade trifluoromethylation/cyclization of unactivated alkene with Langlois reagent as a CF 3 source is described. A variety polycyclic quinazolinones were successfully synthesized in 52–81% yields under transition metal‐ oxidant‐free conditions. The used this strategy possesses the advantages bench‐stablity, cost‐effectivity high‐efficiency. Additionally, gram‐scale reaction, broad substrate scope good functional group tolerance demonstrated synthetic usefulness protocol. magnified image

Language: Английский

Formal Aza‐Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis DOI

Xiangli Yi,

Xile Hu

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(14), P. 4700 - 4704

Published: Jan. 30, 2019

Abstract In oxidative electrochemical organic synthesis, radical intermediates are often oxidized to cations on the way final product formation. Herein, we describe an approach transform electrochemically generated into neutral products by reaction with a metal catalyst. This combines oxidation Cu catalysis effect formal aza‐Wacker cyclization of internal alkenes. The catalyst is essential for transforming secondary and primary alkyl A wide range 5‐membered N‐heterocycles including oxazolidinone, imidazolidinone, thiazolidinone, pyrrolidinone, isoindolinone can be prepared under mild conditions.

Language: Английский

Citations

57

Indirect Electrosynthesis with Halogen Ions as Mediators DOI

Fei Lian,

Kun Xu, Cheng‐Chu Zeng

et al.

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(9), P. 2290 - 2305

Published: March 16, 2021

Abstract Organic electrosynthesis has gained increasing research interest as it harvests electric current redox regents, thereby providing a sustainable alternative to conventional approaches. Compared with direct electrosynthesis, indirect employs mediator(s) lower the overpotentials for substrate activation, and enhance reaction efficiency functional group compatibility by shifting heterogenous electron transfer process be homogenous. As one of most versatile cost‐efficient mediators, halogen mediators are always combined an irreversible halogenation reaction. Thus, electrochemical between substrates doesn't directly controlled two standard potentials difference. In this account, our recent developments in area halogen‐mediated summarized. The anodically generated species from halogenide salts have abilities undergo electron‐transfer (ET) or hydrogen‐atom‐ (HAT) processes. features, scopes, limitations, mechanistic rationalisations discussed account. We hope studies will contribute future broaden scope electrosynthesis.

Language: Английский

Citations

55

Cobalt catalyzed electrochemical [4 + 2] annulation for the synthesis of sultams DOI

Yangmin Cao,

Yong Yuan,

Yueping Lin

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(5), P. 1548 - 1552

Published: Jan. 1, 2020

Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams.

Language: Английский

Citations

51

Electrochemical Installation of CFH2−, CF2H−, CF3−, and Perfluoroalkyl Groups into Small Organic Molecules DOI Creative Commons
Camila M. Kisukuri, Vitor A. Fernandes, José A. C. Delgado

et al.

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(9), P. 2502 - 2525

Published: June 21, 2021

Abstract Electrosynthesis can be considered a powerful and sustainable methodology for the synthesis of small organic molecules. Due to its intrinsic ability generate highly reactive species under mild conditions by anodic oxidation or cathodic reduction, electrosynthesis is particularly interesting otherwise challenging transformations. One such challenge installation fluorinated alkyl groups, which has gained significant attention in medicinal chemistry material science due their unique physicochemical features. Unsurprisingly, several electrochemical fluoroalkylation methods have been established. In this review, we survey recent developments established field mono‐, di‐, trifluoromethylation, perfluoroalkylation

Language: Английский

Citations

48

Electrosynthesis of CF3‐Substituted Polycyclic Quinazolinones via Cascade Trifluoromethylation/Cyclization of Unactivated Alkene DOI
Lei Liu,

Wangqin Zhang,

Chao Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(7), P. 1319 - 1325

Published: Feb. 23, 2022

Abstract An atom and step economy cascade trifluoromethylation/cyclization of unactivated alkene with Langlois reagent as a CF 3 source is described. A variety polycyclic quinazolinones were successfully synthesized in 52–81% yields under transition metal‐ oxidant‐free conditions. The used this strategy possesses the advantages bench‐stablity, cost‐effectivity high‐efficiency. Additionally, gram‐scale reaction, broad substrate scope good functional group tolerance demonstrated synthetic usefulness protocol. magnified image

Language: Английский

Citations

36