Photoelectrochemical Asymmetric Catalysis Enables Enantioselective Heteroarylcyanation of Alkenes via C–H Functionalization

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(34), С. 18753 - 18759

Опубликована: Авг. 15, 2023

The asymmetric difunctionalization of alkenes, a method transforming readily accessible alkenes into enantioenriched chiral structures high value, has long been focal point organic synthesis. Despite tremendous efforts in this domain, it remains considerable challenge to devise enantioselective oxidative dicarbofunctionalization even though these transformations can utilize stable and unfunctionalized functional group donors. In context, we report herein photoelectrocatalytic for the heteroarylcyanation aryl which employs heteroarenes through C-H functionalization. photoelectrochemical catalysis (PEAC) combines photoredox electrocatalysis facilitate formation two C-C bonds operating via hydrogen (H2) evolution obviating need external chemical oxidants.

Язык: Английский

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Recent Advances in Reactions Involving Carbon Dioxide Radical Anion

ACS Catalysis, Год журнала: 2023, Номер 13(24), С. 15991 - 16011

Опубликована: Ноя. 28, 2023

Carbon dioxide radical anion (CO2•–) is a highly reactive nucleophilic species that has recently emerged in organic chemistry as strong single electron donor (reductant) and reactant for the synthesis of carboxylic acids. In general, CO2•– can be generated by either direct reduction CO2 or HAT formate salts. Achievements reactions involving have been witnessed recent years. This Review summarizes advances highlighting some challenges identifying potential areas improvement, which may offer inspiration future studies.

Язык: Английский

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Photoelectrocatalytic C–H amination of arenes

Green Chemistry, Год журнала: 2023, Номер 25(20), С. 7959 - 7962

Опубликована: Янв. 1, 2023

Reported herein is an organocatalyzed photoelectrochemical C(aryl)–H amination reaction for direct access to anilides from easily available and stable arenes carbamates without the need sacrificial oxidants.

Язык: Английский

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Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates

Green Chemistry, Год журнала: 2024, Номер 26(7), С. 4199 - 4208

Опубликована: Янв. 1, 2024

A new photoelectrocatalytic mode permits the synthesis of polycyclic pyrimidin-4-ones through dehydrogenative cyclization malonates with unactivated alkenes.

Язык: Английский

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Visible-light-driven alkene dicarboxylation with formate and CO₂ under mild conditions

Chemical Science, Год журнала: 2024, Номер 15(16), С. 6178 - 6183

Опубликована: Янв. 1, 2024

Low-cost formate salt was used as the reductant and part of carboxyl source in a visible-light-driven dicarboxylation diverse alkenes, including simple styrenes. The highly competing hydrocarboxylation side reaction successfully overridden. Good yields products were obtained under mild conditions at ambient temperature pressure CO

Язык: Английский

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Electroreductive Remote Benzylic C(sp³)–H Arylation of Aliphatic Ethers Using Cyanoarenes for the Synthesis of α-(Hetero)aryl Ethers

Organic Letters, Год журнала: 2024, Номер 26(12), С. 2440 - 2444

Опубликована: Март 19, 2024

An iodoarene-driven electroreductive remote C(sp3)–H arylation of unsymmetrical 1-(o-iodoaryl)alkyl ethers with cyanoarenes for the site selective synthesis α-(hetero)aryl is developed. With introduction as both aryl sources and electron transfer mediators, this method includes an strategy to enable regiocontrollable formation two new bonds, one C(sp2)–H bond, C(sp2)–C(sp3) in a single reaction step through sequence halogen atom (XAT), hydrogen (HAT), radical–radical coupling, decyanation.

Язык: Английский

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Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2352 - 2362

Опубликована: Апрель 5, 2024

Abstract While the emergence of electrophotochemistry provides opportunities, such a chemistry at this stage suffers from limited reaction types and high photocatalyst loadings. A self‐catalyzed electrophotosynthesis as well one with low loading is presented. These external‐oxidant‐free cyclizations are enabling applicable to range activated alkenes, affording diverse array thiocyanato heterocycles including 4‐pyrrolin‐2‐ones, isoquinoline‐1,3‐diones, indolo[2,1‐ ]isoquinolin‐6(5 H )‐ones, benzoimidazo[2,1‐ )‐ones indolin‐2‐ones, protocols amenable late‐stage diversification complex molecular architectures gram‐scale syntheses. Sunlight could serve light source, be conducted in an all‐solar‐driven mode using commercially available photovoltaic panel produce electricity.

Язык: Английский

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Electrophotocatalysis for Organic Synthesis

Chemical Reviews, Год журнала: 2024, Номер 124(21), С. 12264 - 12304

Опубликована: Окт. 23, 2024

Electrocatalysis and photocatalysis have been the focus of extensive research efforts in organic synthesis recent decades, these powerful strategies provided a wealth new methods to construct complex molecules. Despite intense efforts, only recently has there significant on combined use two modalities. Nevertheless, past five years witnessed rapidly growing interest area electrophotocatalysis. This hybrid strategy capitalizes enormous benefits using photons as reagents while also employing an electric potential convenient tunable source or sink electrons. Research this topic led number for C-H functionalization, reductive cross-coupling, olefin addition among others. field seen broad range catalyst types, including both metal organocatalysts. Of particular note work with open-shell photocatalysts, which tend comparatively large redox potentials. Electrochemistry provides means generate such species, making electrophotocatalysis particularly amenable intriguing class catalyst. review surveys applied synthesis, organized broadly into oxidative, reductive, neutral transformations.

Язык: Английский

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Electro-reductive carboxylation of C Cl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO2

Chinese Chemical Letters, Год журнала: 2024, Номер 35(12), С. 110104 - 110104

Опубликована: Июнь 8, 2024

Язык: Английский

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Electroreduction strategy: a sustainable tool for the generation of aryl radicals

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4318 - 4342

Опубликована: Янв. 1, 2024

This review primarily focuses on the generation of aryl radicals via an electroreduction strategy, and systematically elaborates synthetic applications, scope, limitations substrates.

Язык: Английский

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