Photoredox catalysis of acridinium and quinolinium ion derivatives DOI
Shunichi Fukuzumi, Yong‐Min Lee, Wonwoo Nam

et al.

Bulletin of the Korean Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 9, 2024

Abstract Photoredox catalysis has attracted increasing attention because of wide range synthetic transformations and solar energy conversion applications. Reviews on photoredox have so far focused predominantly the This review highlights how organic catalysts were developed they function as efficient photocatalysts in mechanistic point views. In particular, 9‐mesityl‐10‐methylactidinium (Acr + –Mes) been highlighted one best catalysts. Acr –Mes was originally a model compound photosynthetic reaction center to mimic long lifetime charge‐separated state which is converted chemical photosynthesis. The reason why acts most catalyst clarified terms one‐electron redox potentials lifetimes electron‐transfer • •+ ) produced upon photoexcitation different solvents. mesityl substituent at 9‐position moiety essential for discussed comparison with acridinium ions substituents R –R) including 10‐methylacridinium ion no (AcrH ). mechanisms are various reactions mimicking quinolinium its derivatives also that –Mes. Finally, immobilization form composite improve catalytic activity stability.

Language: Английский

Photocatalytic systems: reactions, mechanism, and applications DOI Creative Commons
Farzaneh Mohamadpour, Ali Mohammad Amani

RSC Advances, Journal Year: 2024, Volume and Issue: 14(29), P. 20609 - 20645

Published: Jan. 1, 2024

The photocatalytic field revolves around the utilization of photon energy to initiate various chemical reactions using non-adsorbing substrates, through processes such as single electron transfer, or atom transfer.

Language: Английский

Citations

88
Photoelectrochemical Asymmetric Catalysis Enables Enantioselective Heteroarylcyanation of Alkenes via C–H Functionalization DOI
Xiao‐Li Lai, Hai‐Chao Xu

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(34), P. 18753 - 18759

Published: Aug. 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.

Language: Английский

Citations

63
Molecular Photoelectrocatalysis for Radical Reactions DOI
Peng Xiong, Hai‐Chao Xu

Accounts of Chemical Research, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 13, 2025

ConspectusMolecular photoelectrocatalysis, which combines the merits of photocatalysis and organic electrosynthesis, including their green attributes capacity to offer novel reactivity selectivity, represents an emerging field in chemistry that addresses growing demands for environmental sustainability synthetic efficiency. This synergistic approach permits access a wider range redox potentials, facilitates transformations under gentler electrode decreases use external harsh reagents. Despite these potential advantages, this area did not receive significant attention until 2019, when we others reported first examples modern molecular photoelectrocatalysis. These studies showcased immense hybrid strategy, only inherits strengths its parent fields but also unlocks unprecedented enabling challenging mild conditions while minimizing reliance on stoichiometric oxidants or reductants.In Account, present our efforts develop photoelectrocatalytic strategies leverage homogeneous catalysts facilitate diverse radical reactions. By integrating electrocatalysis with key photoinduced processes such as single electron transfer (SET), ligand-to-metal charge (LMCT), hydrogen atom (HAT), have established methods transform substrates organotrifluoroborates, arenes, carboxylic acids, alkanes into reactive intermediates. intermediates subsequently engage heteroarene C-H functionalization Importantly, photoelectrochemical catalysts, generated bulk solution readily participate efficient reactions without undergoing further overoxidation carbocations, common challenge conventional electrochemical systems.By integration photoelectrocatalysis asymmetric catalysis, developed catalysis (PEAC), proves be enantioselective synthesis chiral nitriles. involves two relay catalytic cycles: initial process engenders benzylic radicals from precursors alkyl aryl alkenes, C-radicals are then subjected cyanation subsequent copper-electrocatalytic cycle.Within realm oxidative transformations, anode serves crucial component recycling generating photocatalyst, cathode promotes proton reduction. dual functionality enables via H

Language: Английский

Citations

3
Photochemistry in Medicinal Chemistry and Chemical Biology DOI
Wenyong Zhu, Claire Empel, Sveva Pelliccia

et al.

Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 67(6), P. 4322 - 4345

Published: March 8, 2024

Photochemistry has emerged as a transformative force in organic chemistry, significantly expanding the chemical space accessible for medicinal chemistry. Light-induced reactions enable efficient synthesis of intricate structures and have found applications throughout different stages drug discovery development processes. Moreover, photochemical techniques provide innovative solutions biology, allowing precise spatiotemporal activation targeted delivery. In this Perspective, we highlight already numerous remarkable even more promising future photochemistry chemistry biology.

Language: Английский

Citations

16
Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates DOI

Minglin Tao,

Feng Qin,

Kaixing Gong

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(7), P. 4199 - 4208

Published: Jan. 1, 2024

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

Language: Английский

Citations

15
Unleashing the potentiality of metals: synergistic catalysis with light and electricity DOI
Zhengjia Shen, Jia‐Lin Tu, Binbin Huang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 4024 - 4040

Published: Jan. 1, 2024

This review provides a comprehensive overview of metal catalysis in photo-electrochemical systems, discussing reaction mechanisms and offering prospects for this triadic catalytic mode.

Language: Английский

Citations

13
Electrophotocatalysis for Organic Synthesis DOI

Matthew C. Lamb,

Keri A. Steiniger, Leslie Trigoura

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(21), P. 12264 - 12304

Published: Oct. 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.

Language: Английский

Citations

11
Photoelectrocatalytic C–H amination of arenes DOI

Zhong‐Wei Hou,

Hong Yan, Jinshuai Song

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 7959 - 7962

Published: Jan. 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.

Language: Английский

Citations

23
Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes DOI

Kaixing Gong,

Yingchun Ma,

Ping Yu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2352 - 2362

Published: April 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.

Language: Английский

Citations

9
Photo‐/Electrocatalytic Difunctionalization of Alkenes Enabled by C‐H Radical Functionalization DOI

Zilong Zhou,

Yin Zhang,

Peizhe Cui

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(62)

Published: Aug. 10, 2024

The difunctionalization of alkenes represents a powerful tool to incorporate two functional groups into the alkene bones for increasing molecular complexity and has been widely utilizations in chemical synthesis. Upon catalysis green, sustainable, mild photo-/electrochemistry technologies, much attentions have attracted development new tactics transformations important alkane feedstocks driven by C-H radical functionalization. Herein, we summarize recent advances photo-/electrocatalytic enabled We detailedly discuss substrate scope mechanisms reactions selecting impressive synthetic examples, which are divided four sections based on final terminated step, including oxidative radical-polar crossover coupling, reductive radical-radical transition-metal-catalyzed coupling.

Language: Английский

Citations

8