Organo‐Mediator Enabled Electrochemical Deuteration of Styrenes

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(45)

Published: Sept. 12, 2023

Despite widespread use of the deuterium isotope effect, selective labeling chemical molecules remains a major challenge. Herein, facile and general electrochemically driven, organic mediator enabled deuteration styrenes with oxide (D2 O) as economical source was reported. Importantly, this transformation could be suitable for various electron rich mediated by triphenylphosphine (TPP). The reaction proceeded under mild conditions without transition-metal catalysts, affording desired products in good yields excellent D-incorporation (D-inc, up to >99 %). Mechanistic investigations means experiments cyclic voltammetry tests provided sufficient support transformation. Notably, method proved powerful tool late-stage biorelevant compounds.

Language: Английский

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Enantioselective Reductive Cross-Couplings of Olefins by Merging Electrochemistry with Nickel Catalysis

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(44), P. 23910 - 23917

Published: Oct. 26, 2023

The merger of electrochemistry and transition metal catalysis has emerged as a powerful tool to join two electrophiles in an enantioselective manner. However, the development electroreductive cross-couplings olefins remains challenge. Inspired by advantages synergistic use with nickel catalysis, we present here Ni-catalyzed cross-coupling acrylates aryl halides alkyl bromides, which affords chiral α-aryl carbonyls good excellent enantioselectivity. Additionally, this catalytic reaction can be applied (hetero)aryl chlorides, is difficult achieve other methods. combination cyclic voltammetry analysis electrode potential studies suggests that NiI species activates oxidative addition bromides single-electron transfer.

Language: Английский

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Electroreduction of unactivated alkenes using water as hydrogen source

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: March 30, 2024

Abstract Herein, we report an electroreduction of unactivated alkyl alkenes enabled by [Fe]-H, which is provided through the combination anodic iron salts and silane generated in situ via cathodic reduction, using H 2 O as H-source. The catalytic amounts Si-additive work H-carrier from to generate a highly active species under continuous electrochemical conditions. This approach shows broad substrate scope good functional group compatibility. In addition hydrogenation, use D instead provides desired deuterated products yields with excellent D-incorporation (up >99%). Further late-stage hydrogenation complex molecules drug derivatives demonstrate potential application pharmaceutical industry. Mechanistic studies are performed provide support for proposed mechanistic pathway.

Language: Английский

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Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6117 - 6125

Published: April 24, 2024

The first paired electrolysis-enabled arylation of quinoxalin-2(1H)-ones was achieved using cyanoarenes as the reagents. A variety 3-arylquinoxalin-2(1H)-ones with various important functional groups were obtained in moderate to good yields under metal- and chemical oxidant-free conditions. With a pair reductive oxidative processes occurring among substrates reaction intermediates, power consumption can be dramatically reduced.

Language: Английский

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Recent Advances in Photochemical/Electrochemical Carboxylation of Olefins with CO₂

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(18), P. 2249 - 2266

Published: May 15, 2024

Comprehensive Summary CO 2 is an abundant, nontoxic, and renewable C1 feedstock in synthetic chemistry. Direct carboxylation of readily available olefins incorporating regarded as a promising strategy to access high value‐added carboxylic acids well fixation. However, due the thermodynamic stability kinetic inertness difficulty controlling regioselectivity, with still remains challenging. Radical‐type functionalization represented powerful protocol enabled development novel transformations this realm. More recently, advance new technology, such photoredox catalysis renaissance electrochemistry organic synthesis, offered unique chemical reactivities radical precursors provided solutions olefins. This review presents recent advances radical‐type olefins, which has mainly been achieved through photocatalysis electrocatalysis last decade. In article, we provide comprehensive introduction progress, summarize advantages limitations current research, discuss potential outlook for further development. Key Scientists

Language: Английский

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Quinone-mediated hydrogen anode for non-aqueous reductive electrosynthesis

Nature, Journal Year: 2023, Volume and Issue: 623(7985), P. 71 - 76

Published: Aug. 21, 2023

Language: Английский

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Electrochemical NiH‐Catalyzed C(sp³)−C(sp³) Coupling of Alkyl Halides and Alkyl Alkenes

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(44)

Published: Sept. 14, 2023

Herein, an electrochemically driven NiH-catalyzed reductive coupling of alkyl halides and alkenes for the construction Csp3 -Csp3 bonds is firstly reported. Notably, serve dual function as substrates hydrogen sources to generate NiH species under electrochemical conditions. The tunable nature this reaction realized by introducing intramolecular coordinating group substrate, where product can be easily adjusted give desired branched products. method proceeds mild conditions, exhibits a broad substrate scope, affords moderate excellent yields with over 70 examples, including late-stage modification natural products drug derivatives. Mechanistic insights offer evidence process. sp3 -carbon-halogen activated through single electron transfer (SET) nickel catalyst in its low valence state, generated cathodic reduction, generation from pivotal transformation.

Language: Английский

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Electrochemical C−H deuteration of pyridine derivatives with D2O

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 7, 2024

Herein, we develop a straightforward, metal-free, and acid-/base-free electrochemical C4-selective C - H deuteration of pyridine derivatives with economic convenient D

Language: Английский

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Electrochemical Multicomponent Cascade Reaction for the Synthesis of Selenazol-2-amines with Elemental Selenium

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4113 - 4119

Published: March 6, 2024

The first example of an electrochemical multicomponent synthesis selenium-containing compounds with inexpensive and abundant elemental selenium as the selenating reagent was developed. A variety selenazol-2-amines were constructed in high yields good functional group tolerance under metal-free chemical oxidant-free conditions.

Language: Английский

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The electrochemical coupling reactions of organic halides compound in a valuable and practical manner for C C and C–heteroatom formation: An overview

Arabian Journal of Chemistry, Journal Year: 2024, Volume and Issue: 17(8), P. 105822 - 105822

Published: May 24, 2024

Owing to the environmental and energy problems nowadays, one of enormous challenges is expanding clean, renewable reduce destructive ecological effects chemical industries. Compared with other traditional processes, electrochemical method has some benefits, such as being selective, causing minor waste, working under mild conditions no external oxidizing or reducing reagents, making this approach more economical eco-friendly. Electrochemistry represents a powerful tool within synthetic organic chemistry. The development part chemistry intends performance reactions employing electrons, including adding removing electrons. Using electric current reagent advantages, simplicity reactions, accessibility materials, replacing toxic applying an eco-friendly environment. During last decades, there been much effort decrease usage fossil fuels, electricity emerged common source. conversion into leads new paths, naturally safe environmentally friendly. Developing electrochemistry approaches for performing high-performance essential reaction green strategy because utilization instead stoichiometric oxidants reductants. Due its helpful friendly ability produce reactive intermediates, advanced considerably in oxidative hydrogen evolution coupling sacrificial anode electroreduction. New developments focus on developing electrolytic catalysts,photoelectrocatalysis, bioelectrosynthesis, optimizing electrode paired electrolysis, artificial intelligence-assisted electrosynthesis. Thus, daily significant number construction projects possibilities electrochemistry. Electrochemical methods constructing compounds have tolerated renewal past decades. Organic wealthy background synthesis. We hope review helps attract attention from researchers by using processes laboratory industrial centers, which pollution create In review, organohalides synthesizing various products summarized discussed since 2000.

Language: Английский

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