4.7 Article

Visible-Light-Induced Radical Type Ring-Opening of Sulfonium Salts with Heteroarenes by Copper Photocatalyst

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Review Chemistry, Organic

Alkylation Reactions with Alkylsulfonium Salts

Ze-Yu Tian et al.

Summary: The application of alkylsulfonium salts as alkyl-transfer reagents in organic synthesis has reemerged. They can readily alkylate various nucleophiles, alkenes, arenes, alkynes, organometallic reagents, etc., and offer convenience, high efficiency, readily accessible and structurally diversified alkylation reagents, good functional group tolerance, and a wide range of substrate types.

SYNTHESIS-STUTTGART (2022)

Article Chemistry, Multidisciplinary

Metal-free allylic C-H nitrogenation, oxygenation, and carbonation of alkenes by thianthrenation

Ming-Shang Liu et al.

Summary: A transition-metal-free protocol for selective allylic C-H nitrogenation, oxygenation, and carbonation of alkenes has been developed, providing multialkyl substituted allylic amines, ammonium salts, sulfonyl amides, esters, and ethers in good yields. The reaction shows excellent functional group tolerance and can be applied to the late-stage allylation of natural products, drug molecules, and peptides with high chemoselectivity.

CHEMICAL SCIENCE (2022)

Article Chemistry, Organic

A desulphurization strategy for Sonogashira couplings by visible light/copper catalysis

Xuan Li et al.

Summary: The development of a new copper-based catalyst for visible-light promoted Sonogashira coupling reactions has been successful, resulting in various substituted alkynes from simple sulfonium salts. This study broadens the limited strategies of copper photocatalysts in organic transformations.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Organic

Site-Selective Late-Stage C-H Functionalization via Thianthrenium Salts

Florian Berger et al.

Summary: C-H functionalization is an efficient method to increase the complexity of organic molecules rapidly, but improving selectivity remains a challenge. By utilizing sulfonium salts, we have developed a highly selective approach for aromatic C-H functionalization, enhancing not only the efficiency of the reaction but also expanding the scope of follow-up reactions.

SYNLETT (2022)

Article Chemistry, Multidisciplinary

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

Jing Fang et al.

Summary: This study describes the alkylation and arylation reactions of sulfonium ylides under transition-metal free conditions. The reaction patterns can be controlled by adjusting the reaction conditions. The method shows excellent substrate compatibility and high product yields under alkaline conditions.

CHINESE CHEMICAL LETTERS (2022)

Article Chemistry, Organic

Nickel-Catalyzed Direct Cross-Coupling of Aryl Sulfonium Salt with Aryl Bromide

Na-Na Ma et al.

Summary: The direct cross-couplings of aryl sulfonium salts with aryl halides using nickel as a reaction catalyst were successfully achieved. The reactions proceeded efficiently via C-S bond activation at ambient temperature, providing moderate to good yields, potentially serving as an attractive alternative to conventional cross-coupling reactions.

ORGANIC LETTERS (2022)

Article Chemistry, Physical

Photoredox-Catalyzed and Copper(II) Salt-Assisted Radical Addition/Hydroxylation Reaction of Alkenes, Sulfur Ylides, and Water

Dong-Mei Yan et al.

Summary: A visible light-driven photoredox-catalyzed and copper(II)-assisted three-component radical addition/hydroxylation reaction of alkenes, sulfur ylides, and water has been reported, providing high-yielding and practical access to valuable gamma-hydroxy carbonyl compounds.

ACS CATALYSIS (2022)

Article Chemistry, Organic

Radial Type Ring Opening of Sulfonium Salts with Dichalcogenides by Visible Light and Copper Catalysis

Wenwen Cui et al.

Summary: In this study, a copper-catalyzed blue-light-induced free radical ring-opening reaction of sulfonium salts with dichalcogenides was developed. The method utilizes an inexpensive copper catalyst and has a broad substrate scope, allowing for the high-yield synthesis of alkyl chalcogenides. This reaction presents a novel ring-opening model for sulfonium salts, breaking the limitation of only nucleophilic ring-opening reactions to form C-heteroatom and C-C bonds.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Palladium Metallaphotoredox-Catalyzed 2-Arylation of Indole Derivatives

Xinmou Wang et al.

Summary: Here, we report a two-step method for the construction of biaryl motifs by combining palladium catalysis and photocatalysis. This mild, dual-catalysis method showed good functional group tolerance and a wide substrate scope, making it suitable for the synthesis of 2-arylindole derivatives and late-stage functionalization of oligopeptides, drugs, and natural products.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Photoredox-catalyzed reaction of thianthrenium salts, sulfur dioxide and hydrazines

Qiangwei Li et al.

Summary: A photoredox-catalyzed three-component reaction was developed to access various arenesulfonohydrazides in moderate to good yields. The reaction exhibited broad substrate scope and excellent functional group compatibility under mild conditions, which was initiated by thianthrenium salts irradiation with visible light.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Multidisciplinary

A general electron donor-acceptor complex for photoactivation of arenes via thianthrenation

Kai Sun et al.

Summary: A new method of photoactivation of electron donor-acceptor complexes between arylsulfonium salts and 1,4-diazabicyclo[2.2.2]octane with visible light or natural sunlight was discovered, enabling the generation of aryl radicals under mild conditions, offering a novel opportunity for two-step para-selective C-H functionalization of complex arenes.

CHEMICAL SCIENCE (2022)

Review Chemistry, Multidisciplinary

A leap forward in sulfonium salt and sulfur ylide chemistry

Rong Fan et al.

Summary: Sulfonium salts and sulfur ylides are important S(IV) motifs with unique reactivities for synthesizing sulfur containing compounds. Significant developments have been observed in this field in recent years. This review aims to provide a concise overview of the recent advances in sulfonium salt and sulfur ylide chemistry.

CHINESE CHEMICAL LETTERS (2021)

Article Chemistry, Organic

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

Qiuli Yan et al.

Summary: An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported, using a single ligand Cu-I photocatalyst formed in situ for the transformation. Diverse organosulfones were obtained in moderate to good yields, demonstrating a promising approach toward the synthesis of diverse and useful organosulfones.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis

Cheng Chen et al.

Summary: Alkyl thianthrenium salts have been synthesized as reliable alkylation reagents, which can readily engage in copper-catalyzed Sonogashira and Kumada reactions to build C(sp(3))-C(sp) bonds under mild photochemical conditions. The method demonstrates great functional breadth and compatibility, even with sensitive Cl, Br, and I atoms.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Photoinduced Copper-Catalyzed Asymmetric C-O Cross-Coupling

Jun Chen et al.

Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Review Chemistry, Organic

Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

Yang Xiong et al.

Summary: Visible-light-mediated copper photocatalysis has become an attractive strategy for constructing basic bonds in an ecologically benign and cost-effective fashion. The intense activity in this area has led to rapid development and expansion of applications, showcasing the high flexibility and potential of copper complexes as standalone photocatalysts in organic reactions.

SYNTHESIS-STUTTGART (2021)

Article Chemistry, Multidisciplinary

Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles

Junting Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Synthesis, Structure, and Reactivity of 5-(Aryl)dibenzothiophenium Triflates

Kevin Kafuta et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Applied

Radical C-C Bond Formation using Sulfonium Salts and Light

Aron Peter et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Review Chemistry, Inorganic & Nuclear

Synthetic Applications of Sulfonium Salts

Sergei I. Kozhushkov et al.

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (2020)

Review Chemistry, Applied

Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur

Thanh Binh Nguyen

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Chemistry, Organic

Thianthrenation-Enabled α-Arylation of Carbonyl Compounds with Arenes

Xiao-Xue Nie et al.

ORGANIC LETTERS (2020)

Review Chemistry, Multidisciplinary

Photoinduced deaminative strategies: Katritzky salts as alkyl radical precursors

Jose Tiago M. Correia et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Physical

Palladium-Catalyzed Borylation of Aryl Sulfoniums with Diborons

Hiroko Minami et al.

ACS CATALYSIS (2018)

Article Chemistry, Multidisciplinary

Photoinduced Copper-Catalyzed Coupling of Terminal Alkynes and Alkyl Iodides

Avijit Hazra et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence

Miles H. Aukland et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Diverse ring opening of thietanes and other cyclic sulfides: an electrophilic aryne activation approach

Tianyu Zheng et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

An aryne triggered ring-opening fluorination of cyclic thioethers with potassium fluoride

Rong Fan et al.

CHEMICAL COMMUNICATIONS (2018)

Review Chemistry, Multidisciplinary

Photoredox Catalysis for Building C-C Bonds from C(sp(2))-H Bonds

Chang-Sheng Wang et al.

CHEMICAL REVIEWS (2018)

Article Chemistry, Organic

Application of arylsulfonium salts as arylation reagents

Ze-Yu Tian et al.

TETRAHEDRON LETTERS (2018)

Review Chemistry, Multidisciplinary

Photocatalytic Activation of Less Reactive Bonds and Their Functionalization via Hydrogen-Evolution Cross-Couplings

Bin Chen et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

Article Chemistry, Organic

Sonogashira Reaction Using Arylsulfonium Salts as Cross-Coupling Partners

Ze-Yu Tian et al.

ORGANIC LETTERS (2017)

Review Chemistry, Multidisciplinary

Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond

Jia-Rong Chen et al.

ACCOUNTS OF CHEMICAL RESEARCH (2016)

Review Chemistry, Multidisciplinary

Heteroleptic Cu-Based Sensitizers in Photoredox Catalysis

Augusto C. Hernandez-Perez et al.

ACCOUNTS OF CHEMICAL RESEARCH (2016)

Article Chemistry, Multidisciplinary

Palladium-catalyzed Mizoroki-Heck-type reactions of [Ph2SRfn][OTf] with alkenes at room temperature

Shi-Meng Wang et al.

CHEMICAL COMMUNICATIONS (2016)

Article Multidisciplinary Sciences

Asymmetric copper-catalyzed C-N cross-couplings induced by visible light

Quirin M. Kainz et al.

SCIENCE (2016)

Article Chemistry, Multidisciplinary

Palladium-Assisted Aromatic Metamorphosis of Dibenzothiophenes into Triphenylenes

Dhananjayan Vasu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Multidisciplinary

Copper-Catalyzed C-H Functionalization Reactions: Efficient Synthesis of Heterocycles

Xun-Xiang Guo et al.

CHEMICAL REVIEWS (2015)

Review Chemistry, Applied

Visible-Light Photocatalytic Reduction of Sulfonium Salts as a Source of Aryl Radicals

Simon Donck et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

Review Chemistry, Multidisciplinary

Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis

Christopher K. Prier et al.

CHEMICAL REVIEWS (2013)

Article Chemistry, Multidisciplinary

Scaffold-hopping strategy toward calanolides with nitrogen-containing heterocycles

Xiao-Yong Guo et al.

CHINESE CHEMICAL LETTERS (2013)

Review Chemistry, Organic

Sulfoxonium and Sulfonium Ylides as Diazocarbonyl Equivalents in Metal-Catalyzed Insertion Reactions

Antonio C. B. Burtoloso et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2013)

Review Chemistry, Organic

New synthetic capabilities of sulfonium salts

VG Nenaidenko et al.

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY (2003)