Enhancing electrochemical reactions in organic synthesis: the impact of flow chemistry DOI Creative Commons
Morgan Regnier, Clara Vega, Dimitris I. Ioannou

и другие.

Chemical Society Reviews, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Utilizing electrons directly offers significant potential for advancing organic synthesis by facilitating novel reactivity and enhancing selectivity under mild conditions. As a result, an increasing number of chemists are exploring electrosynthesis. However, the efficacy electrochemical transformations depends critically on design cell. Batch cells often suffer from limitations such as large inter-electrode distances poor mass transfer, making flow promising alternative. Implementing cells, however, requires foundational understanding microreactor technology. In this review, we briefly outline applications electrosynthesis before providing comprehensive examination existing reactor technologies. Our goal is to equip with insights needed tailor their meet specific requirements effectively. We also highlight application designs in scaling up processes integrating high-throughput experimentation automation. These advancements not only enhance synthetic community but hold promise both academia industry.

Язык: Английский

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

139

Recent advances in the chemistry of ketyl radicals DOI Creative Commons
Áron Péter,

Soumitra Agasti,

Oliver J. Knowles

и другие.

Chemical Society Reviews, Год журнала: 2021, Номер 50(9), С. 5349 - 5365

Опубликована: Янв. 1, 2021

Ketyl radicals are valuable reactive intermediates for synthesis and used extensively to construct complex, functionalized products from carbonyl substrates. Single electron transfer (SET) reduction of the C[double bond, length as m-dash]O bond aldehydes ketones is classical approach formation ketyl metal reductants archetypal reagents employed. The past decade has, however, witnessed significant advances in generation harnessing radicals. This tutorial review highlights recent, exciting developments chemistry by comparing varied contemporary - example, using photoredox catalysts more approaches use will focus on different strategies radical generation, their creative new synthetic protocols, control enantioselectivity, detailed mechanisms where appropriate.

Язык: Английский

Процитировано

128

Recent Advances in the Synthesis of Difluorinated Architectures from Trifluoromethyl Groups DOI
Feng Zhao, Wenlong Zhou,

Zuo Zuo

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 364(2), С. 234 - 267

Опубликована: Ноя. 29, 2021

Abstract Fluorine‐containing moieties are widely used in the pharmaceutical, agrochemical, and material fields. Thus, these structures of immense interest fields organic synthesis medicinal chemistry. Among various fluorinated groups, difluoromethyl unit has drawn increasing attention due to its unique pharmaceutical properties. In recent years, several methods for difluoromethylated compounds have been rapidly developed. However, most treat aromatic with excess difluoromethylating reagents, which often contain organometallic compounds, so transformations generally less environmentally friendly atom‐economical. this review, we summarize development new motifs or difluoroalkenes from trifluoromethylated trifluoromethyl alkenes via single C( sp 3 )−F bond cleavage. magnified image

Язык: Английский

Процитировано

124

Chromium-Catalyzed Allylic Defluorinative Ketyl Olefin Coupling DOI
Chang Zhang, Zhiyang Lin, Yufei Zhu

и другие.

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(30), С. 11602 - 11610

Опубликована: Июль 22, 2021

Herein we report a chromium-catalyzed allylic defluorinative ketyl olefin coupling between aldehydes and α-trifluoromethyl alkenes, which provides novel efficient access to diverse gem-difluorohomoallylic alcohols. Remarkably, the high chemoselectivity of this reaction enables conversion formyl moiety in presence various easily reducible functionalities including ketone, organohalides, aziridine, sulfone, alkyne, unactivated alkene. The utility method is demonstrated by simple derivatizations attached hydroxyl group products. preliminary mechanistic investigations suggest pathway with rate-limiting C–C forming step followed facile β-fluoro elimination.

Язык: Английский

Процитировано

115

Unlocking the Potential of High-Throughput Experimentation for Electrochemistry with a Standardized Microscale Reactor DOI Creative Commons
Jonas Rein, James R. Annand,

Michael K. Wismer

и другие.

ACS Central Science, Год журнала: 2021, Номер 7(8), С. 1347 - 1355

Опубликована: Авг. 5, 2021

Organic electrochemistry has emerged as an enabling and sustainable technology in modern organic synthesis. Despite the recent renaissance of electrosynthesis, broad adoption synthetic community, especially industrial settings, been hindered by lack general, standardized platforms for high-throughput experimentation (HTE). Herein, we disclose design HT

Язык: Английский

Процитировано

107

A guide to organic electroreduction using sacrificial anodes DOI
Yufeng Li, Li‐Rong Wen, Wei‐Si Guo

и другие.

Chemical Society Reviews, Год журнала: 2023, Номер 52(4), С. 1168 - 1188

Опубликована: Янв. 1, 2023

This review focuses on recent advances in sacrificial anode-enabled organic electroreductions.

Язык: Английский

Процитировано

64

Electroreductive Dicarboxylation of Unactivated Skipped Dienes with CO2 DOI
Wei Zhang, Li‐Li Liao, Li Li

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(23)

Опубликована: Апрель 3, 2023

Carboxylation of easily available alkenes with CO2 is highly important to afford value-added carboxylic acids. Although dicarboxylation activated alkenes, especially 1,3-dienes, has been widely investigated, the challenging unactivated 1,n-dienes (n>3) remains unexplored. Herein, we report first skipped dienes via electrochemistry, affording valuable dicarboxylic Control experiments and DFT calculations support single electron transfer (SET) reduction its radical anion, which followed by sluggish addition SET unstabilized alkyl radicals carbanions nucleophilic attack on give desired products. This reaction features mild conditions, broad substrate scope, facile derivations products promising application in polymer chemistry.

Язык: Английский

Процитировано

62

Electrochemical radical-polar crossover: a radical approach to polar chemistry DOI

Zhoumei Tan,

Haonan Zhang, Kun Xu

и другие.

Science China Chemistry, Год журнала: 2023, Номер 67(2), С. 450 - 470

Опубликована: Ноя. 3, 2023

Язык: Английский

Процитировано

50

Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls DOI

Maorui Wang,

Chengqian Zhang, Chenggang Ci

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(20), С. 10967 - 10973

Опубликована: Апрель 19, 2023

Despite the widespread applications of α-hydroxyalkyl cyclic amines, direct and diverse access to such a class unique vicinal amino alcohols still remains, date, challenge. Here, through strategy electroreductive α-hydroxyalkylation inactive N-heteroarenes with ketones or electron-rich arylaldehydes, we describe room temperature approach for construction which features broad substrate scope, operational simplicity, high chemoselectivity, no need pressurized H2 gas transition metal catalysts. The zinc ion generated from anode oxidation plays crucial role in activation both reactants by decreasing their reduction potentials. electroreduction combination Lewis acids this work is anticipated develop more useful transformations.

Язык: Английский

Процитировано

47

Stereoselective amino alcohol synthesis via chemoselective electrocatalytic radical cross-couplings DOI

Jiawei Sun,

Shuanghu Wang, Kaid C. Harper

и другие.

Nature Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 3, 2025

Язык: Английский

Процитировано

8