Electrochemical oxidative difunctionalization of diazo compounds with two different nucleophiles DOI Creative Commons

Dongfeng Yang,

Zhipeng Guan,

Yanan Peng

и другие.

Nature Communications, Год журнала: 2023, Номер 14(1)

Опубликована: Март 17, 2023

With the fast development of synthetic chemistry, introduction functional group into organic molecules has attracted increasing attention. In these reactions, difunctionalization unsaturated bonds, traditionally with one nucleophile and electrophile, is a powerful strategy for chemical synthesis. this work, we develop different path electrochemical oxidative diazo compounds two nucleophiles. Under metal-free external oxidant-free conditions, series structurally diverse heteroatom-containing hardly synthesized by traditional methods (such as high-value alkoxy-substituted phenylthioacetates, α-thio, α-amino acid derivatives well α-amino, β-amino derivatives) are obtained in synthetically useful yields. addition, procedure exhibits mild reaction excellent functional-group tolerance good efficiency on large-scale Importantly, protocol also amenable to key intermediate bioactive simple practical process.

Язык: Английский

Organic Electrochemistry: Molecular Syntheses with Potential DOI Creative Commons
Cuiju Zhu, Nate W. J. Ang, Tjark H. Meyer

и другие.

ACS Central Science, Год журнала: 2021, Номер 7(3), С. 415 - 431

Опубликована: Март 9, 2021

Efficient and selective molecular syntheses are paramount to

Язык: Английский

Процитировано

573
Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis DOI
Nicholas E. S. Tay, Dan Lehnherr, Tomislav Rovis

и другие.

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2487 - 2649

Опубликована: Ноя. 9, 2021

Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do and catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) enable bond formations not constrained by rules ionic 2 electron (e) mechanisms. Instead, they 1e mechanisms capable bypassing electronic steric limitations protecting group requirements, thus enabling chemists disconnect molecules in new different ways. However, while providing similar intermediates, differ several physical chemistry principles. Understanding those differences can be key designing transformations forging disconnections. This review aims highlight these similarities between comparing their underlying principles describing impact electrochemical photochemical methods.

Язык: Английский

Процитировано

355
A critical review on latest innovations and future challenges of electrochemical technology for the abatement of organics in water DOI Creative Commons
Carlos A. Martínez‐Huitle, Manuel A. Rodrigo,

Ignasi Sirés

и другие.

Applied Catalysis B Environment and Energy, Год журнала: 2023, Номер 328, С. 122430 - 122430

Опубликована: Фев. 4, 2023

Updated water directives and ambitious targets like the United Nations' Sustainable Development Goals (SDGs) have emerged in last decade to tackle scarcity contamination. Although numerous strategies been developed remove pollutants, it is still necessary enhance their effectiveness against toxic biorefractory organic molecules. Comprehensive reviews highlighted appealing features of electrochemical technologies, but much progress has made recent years. In this timely review, a critical discussion on latest innovations perspectives most promising tools for wastewater treatment presented. The work describes performance electrocatalytic anodes direct oxidation, oxidation mediated by electrogenerated active chlorine, reduction as well coupled approaches synchronous anodic cathodic processes combined with homogeneous heterogeneous catalysis. section devoted assessment scale-up issues increase technology readiness level.

Язык: Английский

Процитировано

265
Recent progress in cathodic reduction-enabled organic electrosynthesis: Trends, challenges, and opportunities DOI Creative Commons
Binbin Huang, Zemin Sun, Genban Sun

и другие.

eScience, Год журнала: 2022, Номер 2(3), С. 243 - 277

Опубликована: Апрель 23, 2022

Compared with general redox chemistry, electrochemistry using the electron as a potent, controllable, yet traceless alternative to chemical oxidants/reductants usually offers more sustainable options for achieving selective organic synthesis. With its environmentally benign features gradually being uncovered and studied, electrosynthesis is currently undergoing revival becoming rapidly growing area within synthetic community. Among electrochemical transformations, anodically enabled ones have been far extensively exploited than those driven by cathodic reduction, although both approaches are conceptually attractive. To stimulate development of cathodically reactions, this review summarizes recently developed reductive electrosynthetic protocols, discussing highlighting reaction features, substrate scopes, applications, plausible mechanisms reveal recent trends in area. Herein, reduction-enabled preparative transformations categorized into four types: reduction (1) unsaturated hydrocarbons, (2) heteroatom-containing carbon-based systems, (3) saturated C-hetero or C–C polar/strained bonds, (4) hetero-hetero linkages. Apart from net electroreductive few examples photo-electrosynthesis well paired electrolysis also introduced, which offer opportunities overcome certain limitations improve versatility. The electrochemically driven, transition metal-catalyzed cross-couplings that comprehensively discussed several other reviews not included here.

Язык: Английский

Процитировано

137
Electrochemical Late-Stage Functionalization DOI Creative Commons
Yulei Wang, Suman Dana, Hao Long

и другие.

Chemical Reviews, Год журнала: 2023, Номер 123(19), С. 11269 - 11335

Опубликована: Сен. 26, 2023

Late-stage functionalization (LSF) constitutes a powerful strategy for the assembly or diversification of novel molecular entities with improved physicochemical biological activities. LSF can thus greatly accelerate development medicinally relevant compounds, crop protecting agents, and functional materials. Electrochemical synthesis has emerged as an environmentally friendly platform transformation organic compounds. Over past decade, electrochemical late-stage (eLSF) gained major momentum, which is summarized herein up to February 2023.

Язык: Английский

Процитировано

135
Cathodic Corrosion of Metal Electrodes—How to Prevent It in Electroorganic Synthesis DOI Creative Commons
Tom Wirtanen, Tobias Prenzel, Jean‐Philippe Tessonnier

и другие.

Chemical Reviews, Год журнала: 2021, Номер 121(17), С. 10241 - 10270

Опубликована: Июль 6, 2021

The critical aspects of the corrosion metal electrodes in cathodic reductions are covered. We discuss involved mechanisms including alloying with alkali metals, etching aqueous and aprotic media, formation hydrides organometallics. Successful approaches that have been implemented to suppress reviewed. present several examples from electroorganic synthesis where clever use alloys instead soft neat heavy metals application protective cationic additives allowed successfully exploit these materials as cathodes. Because high overpotential for hydrogen evolution reaction, such cathodes can contribute toward more sustainable green synthetic processes. reported strategies expand applications organic electrosynthesis because a negative regime is accessible within protic media common poisons, e.g., sulfur-containing substrates, compatible strongly diminished side reaction paves way efficient reductive conversions.

Язык: Английский

Процитировано

125
Using waste poly(vinyl chloride) to synthesize chloroarenes by plasticizer-mediated electro(de)chlorination DOI
Danielle E. Fagnani, Dukhan Kim, Sofia I. Camarero

и другие.

Nature Chemistry, Год журнала: 2022, Номер 15(2), С. 222 - 229

Опубликована: Ноя. 14, 2022

Язык: Английский

Процитировано

114
Facile and general electrochemical deuteration of unactivated alkyl halides DOI Creative Commons
Pengfei Li,

Chengcheng Guo,

Siyi Wang

и другие.

Nature Communications, Год журнала: 2022, Номер 13(1)

Опубликована: Июнь 30, 2022

Abstract Herein, a facile and general electroreductive deuteration of unactivated alkyl halides (X = Cl, Br, I) or pseudo-halides OMs) using D 2 O as the economical deuterium source was reported. In addition to primary secondary halides, sterically hindered tertiary chlorides also work very well, affording target deuterodehalogenated products with excellent efficiency incorporation. More than 60 examples are provided, including late-stage dehalogenative natural products, pharmaceuticals, their derivatives, all incorporation (up 99% D), demonstrating potential utility developed method in organic synthesis. Furthermore, does not require external catalysts tolerates high current, showing possible use industrial applications.

Язык: Английский

Процитировано

105
Metal‐Free Electrochemical Carboxylation of Organic Halides in the Presence of Catalytic Amounts of an Organomediator DOI
Yanwei Wang, Zhiwei Zhao, Deng Pan

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(41)

Опубликована: Авг. 26, 2022

Herein, an electroreductive carboxylation of organic carbon-halogen bonds (X=Br and Cl) promoted by catalytic amounts naphthalene as mediator is reported. This transformation proceeds smoothly under mild conditions with a broad substrate scope 59 examples, affording the valuable versatile carboxylic acids in moderate to excellent yields without need costly transition metal, wasted stoichiometric metal reductants, or sacrificial anodes. Further late-stage carboxylations natural product drug derivatives demonstrate its synthetic utility. Mechanistic studies confirmed activation via single-electron transfer key role this reaction.

Язык: Английский

Процитировано

84
Electrocarboxylation of Aryl Epoxides with CO2for the Facile and Selective Synthesis of β‐Hydroxy Acids DOI
Yanwei Wang,

Shunyao Tang,

Guoqing Yang

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(38)

Опубликована: Июль 30, 2022

Abstract Herein, an efficient and facile approach to valuable β‐hydroxy acid derivatives from readily available aryl epoxides CO 2 with high chemo‐ regioselectivity under mild sustainable electrochemical conditions is described. This showed broad substrate scope good functional‐group compatibility. In addition epoxides, four‐ six‐membered cyclic ethers could all be tolerated in the reaction provide synthetically useful hydroxy acids efficiency. Further late‐stage carboxylation of complex molecules drug demonstrated its potential application pharmaceutical industry. Mechanistic studies disclosed possible pathways.

Язык: Английский

Процитировано

74