Organic Electrochemistry: Molecular Syntheses with Potential

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

---

Electro-organic synthesis – a 21^stcentury technique

Chemical Science, Год журнала: 2020, Номер 11(46), С. 12386 - 12400

Опубликована: Янв. 1, 2020

This perspective provides insight into recent electro-organic methods and general trends in this field, opens up prospects for future viewpoints.

Язык: Английский

---

New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry

ACS Central Science, Год журнала: 2020, Номер 6(8), С. 1317 - 1340

Опубликована: Июль 16, 2020

As the breadth of radical chemistry grows, new means to promote and regulate single-electron redox activities play increasingly important roles in driving modern synthetic innovation. In this regard, photochemistry electrochemistry-both considered as niche fields for decades-have seen an explosive renewal interest recent years gradually have become a cornerstone organic chemistry. Outlook article, we examine current state-of-the-art areas electrochemistry photochemistry, well nascent area electrophotochemistry. These techniques employ external stimuli activate molecules imbue privileged control reaction progress selectivity that is challenging traditional chemical methods. Thus, they provide alternative entries known reactive intermediates enable distinct strategies were previously unimaginable. Of many hallmarks, electro- are often classified "green" technologies, promoting reactions under mild conditions without necessity potent wasteful oxidants reductants. This reviews most growth these with special emphasis on conceptual advances given rise enhanced accessibility tools trade.

Язык: Английский

---

Making electrochemistry easily accessible to the synthetic chemist

Green Chemistry, Год журнала: 2020, Номер 22(11), С. 3358 - 3375

Опубликована: Янв. 1, 2020

This tutorial bridges an important knowledge gap by providing easily accessible introduction that enables synthetic chemists to explore electrochemistry.

Язык: Английский

---

Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes

Chemistry - A European Journal, Год журнала: 2019, Номер 26(15), С. 3241 - 3246

Опубликована: Дек. 25, 2019

Electrophotochemistry has enabled arene C-H trifluoromethylation with the Langlois reagent CF3 SO2 Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant-free approach for generation radical. electrophotochemistry was carried out in an operationally simple manner, setting stage challenging trifluoromethylations unactivated arenes heteroarenes. robust nature electrophotochemical manifold reflected by wide scope, including electron-rich electron-deficient benzenes, as well naturally occurring Electrophotochemical further achieved flow modular electro-flow-cell equipped in-operando monitoring unit on-line flow-NMR spectroscopy, providing support single electron transfer processes.

Язык: Английский

---

Electrochemical generation of nitrogen-centered radicals for organic synthesis

Green Synthesis and Catalysis, Год журнала: 2021, Номер 2(2), С. 165 - 178

Опубликована: Март 29, 2021

There is a resurgence of interests in organic electrochemistry, which generally accepted as green synthetic tool. In this context, many electrochemical methods have been developed the past decade to access various nitrogen-centered radicals (NCRs) from readily available precursors controlled fashion, enabling rapid development NCR-mediated new reactions for construction nitrogen-containing compounds. review, recent advances chemistry electrochemically generated NCRs are critically highlighted, based on strategies their formation and types NCRs. Focus put mechanism generation different applications.

Язык: Английский

---

Electrochemical Late-Stage Functionalization

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

---

Electrophotocatalytic C−H Heterofunctionalization of Arenes

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(20), С. 11163 - 11167

Опубликована: Март 4, 2021

The electrophotocatalytic heterofunctionalization of arenes is described. Using 2,3-dichloro-5,6-dicyanoquinone (DDQ) under a mild electrochemical potential with visible-light irradiation, undergo oxidant-free hydroxylation, alkoxylation, and amination high chemoselectivity. In addition to batch reactions, an recirculating flow process demonstrated, enabling the conversion benzene phenol on gram scale.

Язык: Английский

---

Cu-Electrocatalytic Diazidation of Alkenes at ppm Catalyst Loading

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(27), С. 11980 - 11985

Опубликована: Июнь 30, 2022

The 1,2-diamine motif is prevalent in natural products, small-molecule pharmaceuticals, and catalysts for asymmetric synthesis. Transition metal catalyzed alkene diazidation has evolved to be an attractive strategy access vicinal primary diamines but remains challenging, especially practical applications, due the restriction a certain type of olefins, frequent use chemical oxidants, requirement high loadings (1 mol % or above). Herein we report scalable Cu-electrocatalytic reaction with 0.02 (200 ppm) copper(II) acetylacetonate as precatalyst without exogenous ligands. In addition its low catalyst loading, electrocatalytic method scalable, compatible broad range functional groups, applicable α,β-unsaturated carbonyl compounds mono-, di-, tri-, tetrasubstituted unactivated alkenes.

Язык: Английский

---

Electrooxidative palladium- and enantioselective rhodium-catalyzed [3 + 2] spiroannulations

Chemical Science, Год журнала: 2022, Номер 13(9), С. 2783 - 2788

Опубликована: Янв. 1, 2022

Despite indisputable progress in the development of electrochemical transformations, electrocatalytic annulations for synthesis biologically relevant three-dimensional spirocyclic compounds has as yet not been accomplished. In sharp contrast, herein, we describe palladaelectro-catalyzed C-H activation/[3 + 2] spiroannulation alkynes by 1-aryl-2-naphthols. Likewise, a cationic rhodium(iii) catalyst was shown to enable electrooxidative [3 spiroannulations via formal C(sp3)-H activations. The versatile featured broad substrate scope, employing electricity green oxidant lieu stoichiometric chemical oxidants under mild conditions. An array enones and diverse spiropyrazolones, bearing all-carbon quaternary stereogenic centers were thereby accessed user-friendly undivided cell setup, with molecular hydrogen sole byproduct.

Язык: Английский

---