Photoexcited Palladium-Initiated Remote Desaturation of N-Alkoxypyridinium Salts DOI
Weiwei Jin, Shouyun Yu

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(21), С. 14715 - 14722

Опубликована: Окт. 11, 2022

1,5-Hydrogen atom transfer (HAT) is an effective strategy to achieve remote desaturation of nonfunctionalized alkanes. Herein, we report a photoinduced reaction N-alkoxypyridinium salts, which serve as alkoxyl radical precursors. Mechanistic studies show that single electron between the excited palladium complex and salt initiates chain process leading salts. This mechanism supported by measurement quantum yield this (Φ = 82). applicable range including some molecule-derived ones.

Язык: Английский

Photoactive Copper Complexes: Properties and Applications DOI
Jérôme Beaudelot, Samuel Oger, Stefano Peruško

и другие.

Chemical Reviews, Год журнала: 2022, Номер 122(22), С. 16365 - 16609

Опубликована: Ноя. 9, 2022

Photocatalyzed and photosensitized chemical processes have seen growing interest recently become among the most active areas of research, notably due to their applications in fields such as medicine, synthesis, material science or environmental chemistry. Among all homogeneous catalytic systems reported date, photoactive copper(I) complexes been shown be especially attractive, not only alternative noble metal complexes, extensively studied utilized recently. They are at core this review article which is divided into two main sections. The first one focuses on an exhaustive comprehensive overview structural, photophysical electrochemical properties mononuclear typical examples highlighting critical structural parameters impact being presented enlighten future design complexes. second section devoted application (photoredox catalysis organic reactions polymerization, hydrogen production, photoreduction carbon dioxide dye-sensitized solar cells), illustrating progression from early current state-of-the-art showcasing how some limitations can overcome with high versatility.

Язык: Английский

Процитировано

205

Energy transfer photocatalysis: exciting modes of reactivity DOI
Subhabrata Dutta, Johannes E. Erchinger, Felix Strieth‐Kalthoff

и другие.

Chemical Society Reviews, Год журнала: 2024, Номер 53(3), С. 1068 - 1089

Опубликована: Янв. 1, 2024

Leveraging light energy to expose the ‘dark’ reactive states describes whole essence of triplet–triplet transfer. This offers an impressive opportunity conduct a multitude diverse reactions and access sought-after molecular motifs.

Язык: Английский

Процитировано

152

Light-empowered contra-thermodynamic stereochemical editing DOI

Peng‐Zi Wang,

Wen‐Jing Xiao, Jia‐Rong Chen

и другие.

Nature Reviews Chemistry, Год журнала: 2022, Номер 7(1), С. 35 - 50

Опубликована: Ноя. 16, 2022

Язык: Английский

Процитировано

78

Enantioselective alkylation of α-amino C(sp3)−H bonds via photoredox and nickel catalysis DOI
Jian Li,

Bu‐Qing Cheng,

Xiaomin Shu

и другие.

Nature Catalysis, Год журнала: 2024, Номер 7(8), С. 889 - 899

Опубликована: Июль 4, 2024

Язык: Английский

Процитировано

19

Elaborating E/Z‐Geometry of Alkenes via Cage‐Confined Arylation Catalysis of Terminal Olefins DOI

Yuanfan Wang,

Jie Chen, Jie Yang

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(25)

Опубликована: Апрель 15, 2023

Abstract A visible light photosensitizing metal‐organic cage is applied as an artificial supramolecular reactor to control the reaction of aryl radicals with terminal olefins under green light/solvent conditions, which facilitates selective transformation in confined enzyme‐mimicking environment give a series geometrically defined E / Z ‐alkenes. The hydrophobic displays good host–guest inclusion aromatic substrates, promoting Meerwein arylation and protecting ‐isomeric products during reaction; while small amount benzonitrile can turn on efficient → isomerization. Besides π–π stacking, hydrogen bonding halogen interactions also act forces for aliphatic known poor acceptors classic arylation. application this switchable cage‐confined catalysis has been demonstrated by syntheses Tapinarof marine natural product from same substrate via controllable selectivity.

Язык: Английский

Процитировано

33

Photoexcited Palladium-Catalyzed Deracemization of Allenes DOI

Changhua Song,

Xiangbin Bai,

Bo Li

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(30), С. 21137 - 21146

Опубликована: Июль 18, 2024

The different enantiomers of specific chiral molecules frequently exhibit disparate biological, physiological, or pharmacological properties. Therefore, the efficient synthesis single is particular importance not only to pharmaceutical sector but also other industrial sectors, such as agrochemical and fine chemical industries. Deracemization, a process during which racemic mixture converted into nonracemic product with 100% atom economy theoretical yield, most straightforward method access enantioenriched challenging task due decrease in entropy microscopic reversibility. Axially allenes bear distinctive structure two orthogonal cumulative π-systems are acknowledged synthetically versatile synthons organic synthesis. selective creation axially high optical purity under mild reaction conditions has always been very popular hot topic remains challenging. Herein, photoexcited palladium-catalyzed deracemization nonprefunctionalized disubstituted disclosed. This provides an economical strategy accommodate broad scope good enantioselectivities yields (53 examples, up 96% yield 95% ee). use suitable palladium complex visible light irradiation essential factor achieving this transformation. A metal-to-ligand charge transfer mechanism was proposed based on control experiments density functional theory calculations. Quantum mechanical studies implicate dual modes asymmetric induction behind our new protocol: (1) sterically controlled stereoselective binding one allene enantiomer ground-state (2) facile, noncovalent interaction-driven excited-state isomerization toward opposite enantiomer. success newly established photochemical should provide inspiration for expansion multisubstituted will open mode enantioselective catalysis.

Язык: Английский

Процитировано

12

Photoinduced Electron Donor Acceptor Complex‐Enabled α‐C(sp3)−H Alkenylation of Amines DOI

Jianzhong Lu,

Kaiyao Yuan,

Jia-Lian Zheng

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(44)

Опубликована: Июль 13, 2024

Allylic amines are prevalent and vital structural components present in many bioactive compounds natural products. Additionally, they serve as valuable intermediates building blocks, with wide-ranging applications organic synthesis. However, direct α-C(sp

Язык: Английский

Процитировано

10

Visible-Light-Induced Excited-State Copper Catalysis: Recent Advances and Perspectives DOI
Nian Li, Bo Li, Kathiravan Murugesan

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(16), С. 11974 - 11989

Опубликована: Июль 26, 2024

Photoactive copper complexes have gained significant attention due to their photocatalytic activities. Different homogeneous Cu(I) complexes, Cu(II) and heterogeneous copper-based photocatalysts been investigated utilized in a broad spectrum of organic transformations. These applications span radical additions, C–C bond C–heteroatom cross-couplings, aerobic oxidative reactions, kinetic resolutions. This review summarizes the advancements this dynamic field visible-light-induced, excited-state copper-catalyzed reactions over recent years. It is organized according type excited species involved provides perspective on current future developments.

Язык: Английский

Процитировано

9

Photoexcited Copper-Catalyzed Enantioselective Allylic C(sp3)–H Acyloxylation of Acyclic Internal Alkenes DOI
Sheng Tang, Hui Xu, Yanfeng Dang

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(39), С. 27196 - 27203

Опубликована: Сен. 17, 2024

The functionalization of C-H bonds streamlines the synthesis complex molecules by eliminating need for substrate preactivation. Traditionally, Kharasch-Sosnovsky reaction, which directly oxidizes allylic into esters under copper catalysis, has been hampered long reaction times, limited scope, and low enantioselectivity with acyclic olefins. Herein, we present a novel, visible light-driven, copper-catalyzed asymmetric that overcomes these challenges. This method expands scope to include internal alkenes improves conditions using eco-friendly light catalysis. It enhances radical reactivity achieves superior regioselectivity in producing acyloxylation products. breakthrough significantly advances direct techniques, offering more efficient sustainable approach synthesizing chiral molecules.

Язык: Английский

Процитировано

8

Kinetic Resolution of α,β-Unsaturated Tertiary Phosphine Oxides via Alkene EZ Isomerization Catalyzed by a Photoexcited Chiral Copper Complex DOI
Liang Liu,

Shiqi Ren,

Xiaohong Gu

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 4541 - 4549

Опубликована: Март 3, 2025

Язык: Английский

Процитировано

1