Radial Type Ring Opening of Sulfonium Salts with Dichalcogenides by Visible Light and Copper Catalysis DOI
Wenwen Cui, Xufeng Li,

Guoju Guo

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(29), P. 5391 - 5396

Published: July 14, 2022

Herein, a copper-catalyzed, blue-light-induced free radical type ring opening of sulfonium salts with dichalcogenides has been initially developed. The developed method features an inexpensive copper catalyst and broad substrate scope, affording practical access to alkyl chalcogenides in high yields. This reaction presents novel ring-opening model salts, which breaks the limitation that only nucleophilic could form C–heteroatom bonds C–C bonds.

Language: Английский

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

et al.

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(22), P. 16365 - 16609

Published: Nov. 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.

Language: Английский

Citations

197
An electron donor–acceptor photoactivation strategy for the synthesis of S-aryl dithiocarbamates using thianthrenium salts under mild aqueous micellar conditions DOI
Hao Xu, Xufeng Li, Jie Ma

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 34(11), P. 108403 - 108403

Published: March 30, 2023

Language: Английский

Citations

50
A General Platform for Visible Light Sulfonylation Reactions Enabled by Catalytic Triarylamine EDA Complexes DOI
Juan D. Lasso, Durbis J. Castillo‐Pazos, Jan Michael Salgado

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(4), P. 2583 - 2592

Published: Jan. 17, 2024

Catalytic electron donor–acceptor (EDA) complexes have recently emerged as a powerful and sustainable alternative to iridium- ruthenium-based photoredox synthetic methods. Yet, these remain underexplored reliant on the use of meticulously designed acceptors that require previous installation. Herein, we report novel EDA complex employing tris(4-methoxyphenyl) amine catalytic donor for sulfonylation alkenes using inexpensive readily available sulfonyl chlorides. Applying this operationally simple, visible-light-mediated general platform, both redox-neutral net-reductive functionalization more than 60 substrates, encompassing vinylic or allylic sulfonylation, hydrosulfonylation, sulfamoylation activated unactivated alkynes.

Language: Английский

Citations

43
1,4‐Aminoarylation of Butadienes via Photoinduced Palladium Catalysis DOI Creative Commons
Yuan Cai,

Gaurav Gaurav,

Tobias Ritter

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(14)

Published: Feb. 9, 2024

Abstract A visible‐light‐induced, three‐component palladium‐catalyzed 1,4‐aminoarylation of butadienes with readily available aryl halides and aliphatic amines has been developed, affording allylamines excellent E ‐selectivity. The reaction exhibits exceptional control over chemo‐, regio‐, stereoselectivity, a broad substrate scope, high functional group compatibility, as demonstrated by the late‐stage functionalization bioactive molecules. Mechanistic investigations are consistent photoinduced radical Pd(0)‐Pd(I)‐Pd(II)‐Pd(0) Heck‐Tsuji–Trost allylation cascade.

Language: Английский

Citations

21
Thianthrenium-enabled sulfonylation via electron donor-acceptor complex photoactivation DOI Creative Commons
Albert Granados, María Jesús Cabrera‐Afonso, Marcos Escolano

et al.

Chem Catalysis, Journal Year: 2022, Volume and Issue: 2(4), P. 898 - 907

Published: April 1, 2022

Sulfone-containing compounds are prevalent building blocks in pharmaceutical agents and other biomolecules, they serve as key intermediates the synthesis of complex scaffolds. During past decade, several methods have been developed to access sulfones. These strategies, however, require use strong reaction conditions, limiting their substrate scope. Recently, visible-light-mediated transformations emerged novel platforms unprecedented structural motifs. This report demonstrates thianthrenium-enabled sulfonylation via intra-complex charge transfer generate transient aryl- persistent sulfonyl radicals that undergo selective coupling alkyl- (hetero)aryl sulfones under ambient conditions. strategy allows retention halide handles, presenting a complementary approach transition metal-mediated photoredox couplings. Furthermore, this high functional group tolerance is amenable late-stage functionalization biomolecules. Mechanistic investigations support intermediacy electron donor-acceptor (EDA) complexes.

Language: Английский

Citations

69
Perovskite as Recyclable Photocatalyst for Annulation Reaction of N-Sulfonyl Ketimines DOI

Anzai Shi,

Kai Sun, Xiaolan Chen

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 24(1), P. 299 - 303

Published: Dec. 16, 2021

A sustainable and cost-effective manner for the photocatalytic annulation reaction of N-sulfonyl ketimines with N-arylglycines to synthesize imidazolidine-fused sulfamidates (31 examples) by employing CsPbBr3 as a heterogeneous photocatalyst has been developed. The catalyst can be simply recovered from mixture reused at least five times without an obvious reduction in its reactivity, exhibiting high economic feature.

Language: Английский

Citations

58
Three-component reaction access to S-alkyl dithiocarbamates under visible-light irradiation conditions in water DOI

Xuehao Li,

Wenwen Cui,

Qirong Deng

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(3), P. 1302 - 1307

Published: Jan. 1, 2022

An environmentally friendly multicomponent reaction protocol to synthesize S -alkyl dithiocarbamate derivatives from Katritzky salt, CS 2 , and secondary amines under visible light irradiation conditions has been developed.

Language: Английский

Citations

48
Thianthrenium-Enabled Phosphorylation of Aryl C–H Bonds via Electron Donor–Acceptor Complex Photoactivation DOI
Hao Xu, Xufeng Li,

Yuzheng Dong

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3784 - 3789

Published: May 16, 2023

An efficient strategy for the preparation of aryl phosphonates via blue-light-promoted single electron transfer process an EDA complex between phosphites and thianthrenium salts has been demonstrated. The corresponding substituted were obtained in good to excellent yields, byproduct thianthrene can be recovered reused quantity. This developed method realizes construction through indirect C-H functionalization arenes, which potential application value drug discovery development.

Language: Английский

Citations

43
One-Metal/Two-Ligand for Dual Activation Tandem Catalysis: Photoinduced Cu-Catalyzed Anti-hydroboration of Alkynes DOI Creative Commons
Javier Corpas, Miguel Gomez‐Mendoza, Jonathan Ramírez-Cárdenas

et al.

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(28), P. 13006 - 13017

Published: July 5, 2022

A dual catalyst system based on ligand exchange of two diphosphine ligands possessing different properties in a copper complex has been devised to merge metal- and photocatalytic activation modes. This strategy applied the formal anti-hydroboration activated internal alkynes via tandem sequence which Cu/Xantphos catalyzes B2pin2-syn-hydroboration alkyne whereas Cu/BINAP serves as photocatalyst for visible light-mediated isomerization resulting alkenyl boronic ester. Photochemical studies by means UV–vis absorption, steady-state time-resolved fluorescence, transient absorption spectroscopy have allowed characterizing photoactive species reaction its interaction with intermediate syn-alkenyl ester through energy transfer from triplet excited state catalyst. In addition, mechanistic shed light into speciation interplay between catalytic cycles critical success factors.

Language: Английский

Citations

40
Visible-Light Photocatalytic Reduction of Aryl Halides as a Source of Aryl Radicals DOI Creative Commons
Jihong Lan, Rongxiang Chen, Fangfang Duo

et al.

Molecules, Journal Year: 2022, Volume and Issue: 27(17), P. 5364 - 5364

Published: Aug. 23, 2022

Aryl- and heteroaryl units are present in a wide variety of natural products, pharmaceuticals, functional materials. The method for reduction aryl halides with ubiquitous distribution is highly sought after late-stage construction various aromatic compounds. visible-light-driven to radicals by electron transfer provides an efficient, simple, environmentally friendly the This review summarizes recent progress generation metal complexes, organic compounds, semiconductors as catalysts, alkali-assisted reaction system. ability mechanism visible light induced systems summarized, intending illustrate comprehensive introduction this research topic readers.

Language: Английский

Citations

39