N‐Oxyl Radicals in Oxidative C–O Coupling: Free‐Radical Hydrogen Substitution and Addition to C=C Bonds DOI
Elena R. Lopat’eva, Igor B. Krylov, Bing Yu

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Abstract N ‐oxyl radicals occupy an important place in free‐radical oxidative CH‐functionalization being one of the most efficient redox‐organocatalysts for hydrogen atom abstraction (HAT). Their applications include aerobic radical chain autoxidation, with formation carbon‐carbon and carbon‐heteroatom bonds. The persistent nature N‐ oxyl combined their high reactivity HAT results unique dual chemistry: same can both propagate reaction (at low concentrations) effectively “terminate” carbon‐centered higher concentrations). latter case opens a new synthetic application area radicals, which they act as abstracting species O‐reagents cross‐coupling thus produced. Apart from C−H bond cleavage, reactive have been extensively used recently C=C double functionalization via addition reactions. In this review, reactions introduction fragments alkene difunctionalizations by oxyls are covered emphasis on relationship between conditions selectivity.

Language: Английский

Electrochemical synthesis: A green & powerful approach to modern organic synthesis and future directions DOI
Sadia Rani, Najoua Sbei, Seyfeddine Rahali

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111216 - 111216

Published: April 1, 2025

Language: Английский

Citations

0

Three-component reaction for the synthesis of imides enabled by electrochemical C(sp3)–H functionalization DOI

Qiao Chu,

Zhaoyue Feng,

Zhang Sumin

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(17), P. 6728 - 6732

Published: Jan. 1, 2023

An electrochemical three-component cascade reaction of aryl acids, nitriles, and alkylbenzenes was developed for the synthesis imides. The products could be applied to synthesize amides, as well primary or tertiary amines.

Language: Английский

Citations

8

Selective α-oxidation of amides via visible-light-driven iron catalysis DOI
Shuhong Liu, Zhichao Dong,

Zhong‐Lin Zang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(6), P. 1205 - 1212

Published: Jan. 1, 2024

Hydroxyl radical-induced selective N -α C(sp 3 )–H bond oxidation of amides was investigated via the visible-light-induced homolysis (VLIH) iron( iii ) complexes.

Language: Английский

Citations

3

Electrochemical C−H/C−C Bond Oxygenation: A Potential Technology for Plastic Depolymerization DOI Creative Commons
Sadia Rani, Samina Aslam, K. B. Lal

et al.

The Chemical Record, Journal Year: 2023, Volume and Issue: 24(3)

Published: Dec. 8, 2023

Herein, we provide eco-friendly and safely operated electrocatalytic methods for the selective oxidation directly or with water, air, light, metal catalyst other mediators serving as only oxygen supply. Heavy metals, stoichiometric chemical oxidants, harsh conditions were drawbacks of earlier oxidative cleavage techniques. It has recently come to light that a crucial stage in deconstruction plastic waste utilization biomass is activation inert C(sp

Language: Английский

Citations

4

Biphasic organic synthesis with continuous electro-flow DOI Creative Commons

Pushpak Mizar,

Sagar Arepally, Thomas Wirth

et al.

Current Opinion in Green and Sustainable Chemistry, Journal Year: 2024, Volume and Issue: 46, P. 100896 - 100896

Published: Feb. 14, 2024

Organic electrochemistry has recently witnessed a renaissance in research as green and cost-efficient method for activating small molecules. Although some of the critical challenges batch electrosynthesis remain, flow can overcome several issues arising from electroorganic systems, such mass transfer, ohmic drop, selectivity. The combination technology with affords practitioners very precise control over reaction conditions, thereby enhancing reproducibility electrochemical processes. use gases chemical reactions synthesis value-added fine chemicals is great significance. This review summarizes recent advances biphasic (gas-liquid) organic synthesis. We summarise examples selective hydrocarbon oxidations using oxygen gas an reactor.

Language: Английский

Citations

1

Electrochemical Decarboxylation/Mumm Rearrangement towards Imides DOI
Ping Jiang,

Chaoqiang Liang,

Tianyu He

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(32)

Published: May 14, 2024

Abstract We report an electrochemically promoted decarboxylation of readily available carboxylic acid and subsequent Mumm rearrangement to synthesize the corresponding imides. The reaction features external oxidant‐free, transition metal‐free mild conditions, good functional group tolerance, affording various imides in moderate yields. Mechanistic studies reveal that selective oxidation aliphatic acids appears be key step this transformation.

Language: Английский

Citations

1

Selective Oxidative Cleavage of Benzyl C–N Bond under Metal-Free Electrochemical Conditions DOI Creative Commons
Jiawei Huang, Xiaoman Li,

Ping Liu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(12), P. 2851 - 2851

Published: June 15, 2024

With the growing significance of green chemistry in organic synthesis, electrochemical oxidation has seen rapid development. Compounds undergo oxidation–reduction reactions through electron transfer at electrode surface. This article proposes use methods to achieve cleavage benzyl C–N bond. method selectively oxidatively cleaves bond without need for metal catalysts or external oxidants. Additionally, primary, secondary, and tertiary amines exhibit good adaptability under these conditions, utilizing water as sole source oxygen.

Language: Английский

Citations

1

Photocatalytic and Electrocatalytic α-C–H Functionalization of Tertiary Amines DOI
Yumeng Liu,

Xiaojian Li,

Jiahong Li

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 166, P. 134234 - 134234

Published: Aug. 31, 2024

Language: Английский

Citations

0

Electrochemically Induced Synthesis of N-Allyloxyphthalimides via Cross-Dehydrogenative C–O Coupling of N-Hydroxyphthalimide with Alkenes Bearing the Allylic Hydrogen Atom DOI Creative Commons
Stanislav A. Paveliev, Oleg O. Segida,

Andrey Dvoretskiy

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: 9(50), P. 49825 - 49831

Published: Dec. 2, 2024

The electrochemically induced reaction between alkenes, bearing an allylic hydrogen atom, and N-hydroxyphthalimide was investigated. Cross-dehydrogenative C–O coupling with phthalimide-N-oxyl radical, derived from N-hydroxyphthalimide, occurs instead of oxidation the site, formation a carbonyl group or functionalization double C═C bond. discovered transformation proceeds in undivided electrochemical cell equipped carbon felt anode platinum cathode. Coupling products were obtained yields up to 79%. developed process is based on abstraction atom position for while bond remains unreacted. method exploits ability radical abstract atoms following interception intermediate C-centered radical.

Language: Английский

Citations

0

Regioselective Intermolecular Hydroamidation of β‐CF3‐1,3‐enynamides: An Approach to Tri‐substituted γ‐CF3‐allenamides DOI

Yuxuan Cao,

Zongxiang Yu,

Yizhen Chen

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(44)

Published: Oct. 14, 2024

Abstract A simple base mediated, highly regioselective 1,4‐hydroamidation of β ‐CF 3 ‐1,3‐enynamides with secondary amides for synthesis tri‐substituted γ ‐allenamides compounds was developed. N ‐alkyl sulfonamides are generally good candidates the present transformation. could be employed potential value‐added such as fluorinated halogenated pyrrole, tetrahydroquinoline and 2‐CF ‐putrescine derivatives.

Language: Английский

Citations

0