4.8 Article

Organoelectrophotocatalytic C-H Silylation of Heteroarenes

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。
Article Multidisciplinary Sciences

Electrophotocatalytic oxygenation of multiple adjacent C-H bonds

Tao Shen et al.

Summary: Oxygen-containing functional groups are found in complex small molecules. The selective oxygenation of contiguous C-H bonds to form multiple C-O bonds has been mainly achieved through biosynthesis. However, this study demonstrates the successful synthetic oxygenation of two or three contiguous C-H bonds using electrophotocatalysis, with high selectivity and avoidance of overoxidation risk.

NATURE (2023)

Article Chemistry, Organic

Electrochemical monofluoroalkylation cyclization of N-arylacrylamides to construct monofluorinated 2-oxindoles

Yanxia Lv et al.

Summary: An electrochemical method for monofluoroalkylation cyclization of N-arylacrylamides to synthesize monofluorinated 2-oxindoles has been developed. This method utilizes dimethyl 2-fluoromalonate as a monofluoroalkyl radical precursor and eliminates the need for prefunctionalized monofluoroalkylation reagents and sacrificial oxidants. Various monofluorinated nitrogen-containing heterocyclic compounds were efficiently obtained with satisfactory yields from easily available materials.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Article Chemistry, Organic

Paired electrochemical C-H bromination of (hetero)arenes with 2-bromoethan-1-ol

Yanxia Lv et al.

Summary: A site-selective electrochemical C-H bromination of (hetero)arenes with 2-bromoethan-1-ol through paired electrolysis is developed, where the anodic oxidation of Br- produced by the cathodic reduction of 2-bromoethan-1-ol is essential. The method shows good compatibility with common functional groups and can be easily scaled up. A variety of brominated products can be obtained with satisfactory yields at room temperature in a simple undivided cell.

ORGANIC CHEMISTRY FRONTIERS (2023)

Article Chemistry, Multidisciplinary

Electrophotocatalytic Si-H Activation Governed by Polarity-Matching Effects

Yangye Jiang et al.

Summary: This study reports a new strategy for homolysis of Si-H bonds using electrooxidation, photoinduced ligand-to-metal charge transfer, and radical-mediated hydrogen atom transfer. This method provides rapid access to Si-functionalized benzimidazo-fused isoquinolinones with broad functional-group compatibility.

CCS CHEMISTRY (2022)

Review Chemistry, Multidisciplinary

Synthetic Molecular Photoelectrochemistry: New Frontiers in Synthetic Applications, Mechanistic Insights and Scalability

Shangze Wu et al.

Summary: Synthetic photoelectrochemistry (PEC) is a new frontier for the generation and handling of reactive intermediates, which allows selective single-electron transfer (SET) reactions in a greener way and expands the possibilities of redox transformations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Organic

Photoinduced Silylation of N-Heteroarenes and Unsaturated Benzamides with Naphthalimide-Based Organic Photocatalysts

Wenjuan Zhang et al.

Summary: This article describes the development of a general strategy for the silylation of N-heteroaromatics and unsaturated benzamides by rationally designing an efficient organic photocatalyst. The process is characterized by its simplicity, mild reaction conditions, and utilization of readily prepared naphthalimide (NI)-based organic photocatalysts. Importantly, both inert trialkylhydrosilanes and arylhydrosilanes are compatible with this protocol.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Electrophotocatalysis: Combining Light and Electricity to Catalyze Reactions

He Huang et al.

Summary: This Perspective highlights recent advances in the area of electrophotocatalysis, which combines the power of light and electrical energy to realize new catalytic transformations. Electrophotocatalysis offers the ability to perform potent yet selective redox reactions under relatively mild conditions, without the need for large quantities of chemical oxidants or reductants.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Organic

Photoredox Metal-Free Allylic Defluorinative Silylation of α-Trifluoromethylstyrenes with Hydrosilanes

Cong Luo et al.

Summary: We have developed an efficient strategy that combines organic photoredox and hydrogen atom transfer to prepare gem-difluoroallylsilanes via defluorinative silylation of alpha-trifluoromethylstyrenes using hydrosilanes as silicon sources. This environmentally friendly approach allows for the preparation of structurally diverse gem-difluoroallylsilanes with excellent functional group compatibility, making it suitable for late-stage modification of bioactive and complex molecules.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Electrochemical Synthesis of gem-Difluoro- and γ-Fluoro-Allyl Boronates and Silanes

Maude Aelterman et al.

Summary: The electrochemical synthesis of fluorinated allyl silanes and boronates was disclosed in this study. By adding electrogenerated boryl or silyl radicals onto various alpha-trifluoromethyl or alpha-difluoromethylstyrenes, a wide range of gem-difluoro and gamma-fluoroallyl boronates and silanes were successfully synthesized. The reactions were also scaled up under continuous flow conditions, demonstrating promising volumetric productivity. The synthetic utility of these building blocks was further highlighted through versatile transformations, and plausible reaction mechanisms were proposed to explain the formation of the products.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

Article Chemistry, Organic

Light-Promoted Arylsilylation of Alkenes with Hydrosilanes

Wanyao Zheng et al.

Summary: In this study, we have reported a light-promoted dual catalysis for arylsilylation of alkenes via radical-radical cross-coupling with various hydrosilanes. This method provides a simple and efficient way to prepare organosilicon compounds with a wide range of substrates and good tolerance towards functional groups under transition-metal- and chemical-oxidant-free conditions. Additionally, the arylsilylation of alkenes can also proceed via a possible electron donor-acceptor complex under exogenous photocatalyst-free conditions.

ORGANIC LETTERS (2022)

Article Chemistry, Physical

Photoelectrochemical asymmetric catalysis enables site- and enantioselective cyanation of benzylic C-H bonds

Chen-Yan Cai et al.

Summary: The combination of molecular photoelectrochemistry and asymmetric catalysis enables highly site- and enantioselective cyanation of benzylic C(sp(3))-H bonds. This photoelectrochemical asymmetric catalysis does not require a chemical oxidant and exhibits exceptional site selectivity and functional group tolerance, allowing efficient conversion of feedstock chemicals and late-stage functionalization of complex bioactive molecules and natural products, including those with multiple benzylic sites.

NATURE CATALYSIS (2022)

Review Chemistry, Organic

Recent advances in photo- and electro-enabled radical silylation

Li-Qing Ren et al.

Summary: This review highlights the recent advances in the field of photo- and electrocatalysis-mediated radical silylation reactions, aiming to inspire further research and applications in this emerging area.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Multidisciplinary

Electrochemical Hydrosilylation of Alkynes

Tony Biremond et al.

Summary: In this study, the electrochemical hydrosilylation of alkynes was reported. Using the Suginome reagent (PhMe2Si-Bpin), a wide range of terminal alkynes and internal alkynes were successfully converted into the hydrosilylated product with high yields and good selectivity towards the linear product. Preliminary mechanistic study suggested the involvement of a silyl radical in the alkyne reaction.

ACS ORGANIC & INORGANIC AU (2022)

Article Chemistry, Multidisciplinary

Selective Electrochemical Hydrolysis of Hydrosilanes to Silanols via Anodically Generated Silyl Cations

Hao Liang et al.

Summary: The study reports the first electrochemical hydrolysis of hydrosilanes to silanols under mild and neutral conditions using NHPI as a mediator, showing moderate to good yields and compatibility with complex molecules. Preliminary mechanistic studies suggest a nucleophilic substitution reaction of an electrogenerated silyl cation with H2O.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Oligosilanes as Silyl Radical Precursors through Oxidative Si-Si Bond Cleavage Using Redox Catalysis

Xiaoye Yu et al.

Summary: This study explores a highly efficient visible-light-mediated hydrosilylation of electron-deficient alkenes through cleavage of a trimethylsilyl-polysilanyl Si-Si bond. The method exhibits broad substrate scope and high functional group tolerance, enabling the construction of functionalized trisilanes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Recent advances in synthesis of organosilicons via radical strategies

Xueping Zhang et al.

Summary: This article reviews the research progress in the synthesis of organosilicon compounds by free radical pathways since 2016, mainly achieved through the reaction of silyl radicals triggered by peroxide, transition-metal-induced peroxide decomposition, alkali, and photocatalysis.

CHINESE CHEMICAL LETTERS (2021)

Article Chemistry, Multidisciplinary

Manganese-catalysed divergent silylation of alkenes

Jie Dong et al.

Summary: This study presents a new method for manganese-catalysed dehydrosilylation and hydrosilylation of alkenes, utilizing a ligand-tuned metalloradical reactivity strategy. The reaction is redox-neutral and atom-economical, with broad substrate scope and excellent functional group tolerance, suitable for various synthetic applications on a gram scale.

NATURE CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Electrochemical Radical Silyl-Oxygenation of Activated Alkenes

Jie Ke et al.

Summary: An efficient electrochemical radical silyl-oxygenation method has been demonstrated for electron-deficient alkenes, providing access to a variety of highly functionalized silicon-containing molecules. The process shows good yields, excellent chemo- and regio-selectivity, and wide substrate scope with high functional-group tolerance, without the need for transition metal catalysts or chemical oxidants. The ability to generate silyl radicals through electrochemical Si-H activation offers new opportunities for the sustainable and green synthesis of valuable organosilicon compounds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Applied

Synthesis of Dibenzosiloles through Electrocatalytic Sila-Friedel-Crafts Reaction

Pan Han et al.

Summary: A novel electrocatalyzed method has been developed for the preparation of dibenzosiloles from biarylhydrosilanes using an intramolecular C-H/Si-H dehydrogenative coupling strategy. Both electro-donating and electro-withdrawing substitution groups were tolerated for this transformation, and the desired dibenzosilole products could be obtained in moderate to excellent yields. A sila-Friedel-Crafts reaction mechanism was proposed based on previous literature and controlled experiments.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Review Chemistry, Multidisciplinary

Electrocatalysis as an enabling technology for organic synthesis

Luiz F. T. Novaes et al.

Summary: Electrochemistry has recently become a versatile strategy in achieving challenging transformations in synthetic organic chemistry. The use of redox-active electrocatalysts has increased in recent developments in electrosynthesis to enhance control over reactive intermediates. Electrocatalytic mediators allow for synthetic transformations to proceed in a manner different from purely chemical methods.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Multidisciplinary

Organic photoredox catalyzed C-H silylation of quinoxalinones or electron-deficient heteroarenes under ambient air conditions

Changhui Dai et al.

Summary: Direct C-H silylation of quinoxalinones was achieved using organic photoredox catalysis and hydrogen atom transfer, under transition metal- and external oxidant-free conditions. A range of silylated quinoxalinones with diverse functional groups were synthesized in moderate to high yields, and the methodology was also applicable to electron-deficient heteroarenes.

GREEN CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Electrochemistry Broadens the Scope of Flavin Photocatalysis: Photoelectrocatalytic Oxidation of Unactivated Alcohols

Wen Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

Metalla-electrocatalyzed C-H Activation by Earth-Abundant 3d Metals and Beyond

Lutz Ackermann

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Review Chemistry, Multidisciplinary

Synthetic Photoelectrochemistry

Joshua P. Barham et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Potent Reductants via Electron-Primed Photoredox Catalysis: Unlocking Aryl Chlorides for Radical Coupling

Nicholas G. W. Cowper et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Reductive Electrophotocatalysis: Merging Electricity and Light To Achieve Extreme Reduction Potentials

Hyunwoo Kim et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Sila- and Germacarboxylic Acids: Precursors for the Corresponding Silyl and Germyl Radicals

Ning-Xin Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry

Jinjian Liu et al.

ACS CENTRAL SCIENCE (2020)

Article Chemistry, Multidisciplinary

Cross-Electrophile Coupling of Unactivated Alkyl Chlorides

Holt A. Sakai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Manganese-Catalyzed Oxidative Azidation of C(sp3)-H Bonds under Electrophotocatalytic Conditions

Linbin Niu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

An Electroreductive Approach to Radical Silylation via the Activation of Strong Si-Cl Bond

Lingxiang Lu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp3)-H Bonds

Fei Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Recent Advances in Minisci-Type Reactions

Rupert S. J. Proctor et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Electrochemical Oxidative Cross-Coupling with Hydrogen Evolution Reactions

Yong Yuan et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

Review Chemistry, Multidisciplinary

Chemistry with Electrochemically Generated N-Centered Radicals

Peng Xiong et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

Article Chemistry, Multidisciplinary

Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication

He Huang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Editorial Material Chemistry, Multidisciplinary

Merging Photocatalysis with Electrochemistry: The Dawn of a new Alliance in Organic Synthesis

Luca Capaldo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Photoelectrochemical C-H Alkylation of Heteroarenes with Organotrifluoroborates

Hong Yan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Photocatalytic C-H silylation of heteroarenes by using trialkylhydrosilanes

Shihui Liu et al.

CHEMICAL SCIENCE (2019)

Review Chemistry, Multidisciplinary

Electrifying Organic Synthesis

Anton Wiebe et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Chemistry, Multidisciplinary

Use of Electrochemistry in the Synthesis of Heterocyclic Structures

Yangye Jiang et al.

CHEMICAL REVIEWS (2018)

Article Chemistry, Multidisciplinary

Dichotomy of Manganese Catalysis via Organometallic or Radical Mechanism: Stereodivergent Hydrosilylation of Alkynes

Xiaoxu Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Organic

Free-Radical-Promoted Site-Selective C-H Silylation of Arenes by Using Hydrosilanes

Zhengbao Xu et al.

ORGANIC LETTERS (2017)

Review Chemistry, Multidisciplinary

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Ming Yan et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

Stereoselective synthesis of vinylsilanes via copper-catalyzed silylation of alkenes with silanes

Jian Gu et al.

CHEMICAL COMMUNICATIONS (2016)

Review Chemistry, Organic

Recent developments in free-radical-promoted C-Si formation via selective C-H/Si-H functionalization

Xiaojie Shang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Review Chemistry, Multidisciplinary

Catalytic Silylation of Unactivated C-H Bonds

Chen Cheng et al.

CHEMICAL REVIEWS (2015)

Review Chemistry, Multidisciplinary

Direct silylation reactions of inert C-H bonds via transition metal catalysis

Yunhui Yang et al.

SCIENCE CHINA-CHEMISTRY (2015)

Article Chemistry, Medicinal

Rings in Drugs

Richard D. Taylor et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

Article Chemistry, Medicinal

Organosilicon Molecules with Medicinal Applications

Annaliese K. Franz et al.

JOURNAL OF MEDICINAL CHEMISTRY (2013)

Review Chemistry, Multidisciplinary

Silicon-based cross-coupling reaction: an environmentally benign version

Yoshiaki Nakao et al.

CHEMICAL SOCIETY REVIEWS (2011)