4.7 Article

Hypervalent-iodine promoted selective cleavage of C(sp3)-C(sp3) bonds in ethers

Related references

Note: Only part of the references are listed.
Article Chemistry, Organic

Photoinduced Ligand-to-Metal Charge Transfer (LMCT) of Fe Alkoxide Enabled C-C Bond Cleavage and Amination of Unstrained Cyclic Alcohols

Ting Xue et al.

Summary: This study reports an alkoxy radical process for the C-C bond cleavage and functionalization of unstrained tertiary and secondary cyclic alcohols. Iron catalysts facilitate alkoxy radical formation and enable the ring opening and amination of cyclic alcohols. The method allows for the synthesis of remote amino carbonyl compounds in a wide scope and with excellent yields under mild conditions.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Electrophotochemical Ce-Catalyzed Ring-Opening Functionalization of Cycloalkanols under Redox-Neutral Conditions: Scope and Mechanism

Zhaoliang Yang et al.

Summary: This study reports a method for the ring-opening functionalization of cycloalkanols using electrophotochemical catalysis. The method allows for selective cleavage of cycloalkanols with different ring sizes while tolerating various functional groups. The presence of chloride enables the selective formation of different types of bonds without the use of external oxidants.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Review Chemistry, Multidisciplinary

Photocatalytic C(sp3) radical generation via C-H, C-C, and C-X bond cleavage

Chia-Yu Huang et al.

Summary: This review presents recent advancements and representative examples in photocatalytic generation of C(sp(3)) radicals (R), categorized into C-H, C-C, and C-X bond cleavages based on key bond cleavages. A general mechanistic scenario and key steps in R formation are discussed in each section.

CHEMICAL SCIENCE (2022)

Review Chemistry, Multidisciplinary

Visible Light-Driven Radical-Mediated C-C Bond Cleavage/Functionalization in Organic Synthesis

Xiao-Ye Yu et al.

Summary: In recent years, visible light photoredox-catalyzed radical-mediated C-C bond cleavage reactions have emerged as a powerful alternative method for overcoming the thermodynamic and kinetic barrier of C-C bond cleavage in diverse molecular scaffolds. These reactions provide an efficient way to construct structurally diverse molecular skeletons, contributing to the development in the field of synthetic organic chemistry.

CHEMICAL REVIEWS (2021)

Review Chemistry, Multidisciplinary

Electrochemical Oxidation Induced Selective C-C Bond Cleavage

Shi-Hui Shi et al.

Summary: Selective C-C bond cleavage using electrochemical methods has been identified as a sustainable and scalable strategy that shows potential in replacing chemical reagents with electricity. Progress in this area has been made, with more examples of C-C bond cleavage via different maneuvers being developed recently, showcasing the exciting potential of electrochemical synthesis.

CHEMICAL REVIEWS (2021)

Editorial Material Chemistry, Multidisciplinary

Introduction: Carbon-Carbon Bond Cleavage in Stereoselective Synthesis

Ilan Marek

CHEMICAL REVIEWS (2021)

Article Chemistry, Multidisciplinary

Mechanistic Investigation of the Iron-Catalyzed Azidation of Alkyl C(sp3)-H Bonds with Zhdankin's λ3-Azidoiodane

Craig S. Day et al.

Summary: The mechanism of azidation of C(sp(3))-H bonds catalyzed by iron(II)(pybox) complexes with Zhdankin's lambda(3)-azidoiodane reagent has been elucidated. Mechanistic experiments show that the azidoiodane reagent undergoes I-N bond homolysis to form radicals that selectively abstract hydrogen atoms from substrates. The alkyl radicals then react with iron(III)azide complexes to form C(sp(3))-N-3 bonds. The catalyst has a significant impact on the rate of product formation and reactant consumption.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Multidisciplinary Sciences

C(sp3)-H methylation enabled by peroxide photosensitization and Ni-mediated radical coupling

Aristidis Vasilopoulos et al.

Summary: The research presents a synthetic method that allows for direct methylation of C(sp(3))-H bonds in drug-like molecules and pharmaceutical building blocks, leading to changes in potency, selectivity, and metabolic stability.

SCIENCE (2021)

Article Chemistry, Multidisciplinary

Depolymerization of Hydroxylated Polymers via Light-Driven C-C Bond Cleavage

Suong T. Nguyen et al.

Summary: This study introduces a catalytic method for depolymerization of commercial phenoxy resin and high molecular weight hydroxylated polyolefin derivatives through light-driven C-C bond cleavage, producing isolable product mixtures that can be diversified into polymer monomers. The hydroxyl group not only controls depolymerization, but also modulates the thermomechanical properties of the materials, offering a new approach for polymer recycling and development of degradable-by-design polyolefin materials.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Copper-Catalyzed Enantioselective Arylation via Radical-Mediated C-C Bond Cleavage: Synthesis of Chiral ω,ω-Diaryl Alkyl Nitriles

Guo-Qing Cui et al.

Summary: The first example of copper-catalyzed ring-opening, enantioselective arylation of cyclic ketoxime esters has been developed with high yield and excellent enantioselectivity. The side-arm bis(oxazoline) ligand plays a significant role in this asymmetric catalytic transformation, providing an efficient route to construct diverse chiral omega,omega-diaryl alkyl nitriles. This synthetic method also demonstrates its utility in further derivatizing the omega,omega-diaryl alkyl nitrile to the corresponding amide.

ORGANIC LETTERS (2021)

Article Multidisciplinary Sciences

Electrochemical C-C bond cleavage of cyclopropanes towards the synthesis of 1,3-difunctionalized molecules

Pan Peng et al.

Summary: The study developed a method for electrochemical C-C bond cleavage and 1,3-difunctionalization of arylcyclopropanes under catalyst-free and external-oxidant-free conditions. By strategically choosing nucleophiles, high chemo- and regioselectivity were achieved in reactions involving 1,3-difluorination, 1,3-oxyfluorination and 1,3-dioxygenation.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Metal-free visible-light-promoted C(sp3)-H functionalization of aliphatic cyclic ethers using trace O2

Ben Niu et al.

Summary: The light-promoted C-C bond forming reaction can yield sulfone and phosphate derivatives at room temperature without the need for metals or photoredox catalyst. This transformation proceeds through an auto-oxidation mechanism maintained by trace amounts of O-2 as the sole green oxidant.

GREEN CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Synthetic Photoelectrochemistry

Joshua P. Barham et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Physical

Light-Driven Depolymerization of Native Lignin Enabled by Proton Coupled Electron Transfer

Suong T. Nguyen et al.

ACS CATALYSIS (2020)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Asymmetric [8+2] Dipolar Cycloadditions of Vinyl Carbamates and Photogenerated Ketenes

Qun-Liang Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Utilizing Vinylcyclopropane Reactivity: Palladium-Catalyzed Asymmetric [5+2] Dipolar Cycloadditions

Miao-Miao Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Organic

Aerobic C-H Functionalization Using Pyrenedione as the Photocatalyst

Yuannian Zhang et al.

SYNTHESIS-STUTTGART (2020)

Article Chemistry, Multidisciplinary

Practical Catalytic Cleavage of C(sp3)-C(sp3) Bonds in Amines

Wu Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Multidisciplinary Sciences

Hydrodealkenylative C(sp3)-C(sp2) bond fragmentation

Andrew J. Smaligo et al.

SCIENCE (2019)

Article Chemistry, Multidisciplinary

Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer

Anamitra Chatterjee et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Biochemistry & Molecular Biology

An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies

Qili Lu et al.

MOLECULES (2019)

Article Chemistry, Multidisciplinary

A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions

Eisuke Ota et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Multidisciplinary

Visible light-driven organic photochemical synthesis in China

Yiyun Chen et al.

SCIENCE CHINA-CHEMISTRY (2019)

Article Chemistry, Physical

Electrochemically Oxidative C-C Bond Cleavage of Alkylarenes for Anilines Synthesis

Yeerlan Adeli et al.

ACS CATALYSIS (2019)

Review Chemistry, Multidisciplinary

Cleavage of carbon-carbon bonds by radical reactions

Paramasivam Sivaguru et al.

CHEMICAL SOCIETY REVIEWS (2019)

Article Chemistry, Multidisciplinary

Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp(3))-H Bonds

Yaxin Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Multidisciplinary Sciences

Deconstructive fluorination of cyclic amines by carbon-carbon cleavage

Jose B. Roque et al.

SCIENCE (2018)

Article Multidisciplinary Sciences

Deconstructive diversification of cyclic amines

Jose B. Roque et al.

NATURE (2018)

Article Multidisciplinary Sciences

Singlet oxygen-mediated selective C-H bond hydroperoxidation of ethereal hydrocarbons

Arunachalam Sagadevan et al.

NATURE COMMUNICATIONS (2017)

Review Chemistry, Multidisciplinary

Metal-Organic Cooperative Catalysis in C-H and C-C Bond Activation

Dong-Su Kim et al.

CHEMICAL REVIEWS (2017)

Review Chemistry, Multidisciplinary

Oxygenation via C-H/C-C Bond Activation with Molecular Oxygen

Yu-Feng Liang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2017)

Review Chemistry, Multidisciplinary

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

James A. Bull et al.

CHEMICAL REVIEWS (2016)

Review Chemistry, Multidisciplinary

Potential of Metal-Catalyzed C-C Single Bond Cleavage for Organic Synthesis

Masahiro Murakami et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Physical

Mechanism of Vanadium-Catalyzed Selective C-O and C-C Cleavage of Lignin Model Compound

Yuan-Ye Jiang et al.

ACS CATALYSIS (2016)

Article Chemistry, Multidisciplinary

Characterizing chain processes in visible light photoredox catalysis

Megan A. Cismesia et al.

CHEMICAL SCIENCE (2015)

Review Chemistry, Multidisciplinary

Selective Carbon-Carbon Bond Cleavage for the Stereoselective Synthesis of Acyclic Systems

Ilan Marek et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Direct α-Arylation of Ethers through the Combination of Photoredox-Mediated C-H Functionalization and the Minisci Reaction

Jian Jin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Multidisciplinary

Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds

Feng Chen et al.

CHEMICAL REVIEWS (2014)

Article Multidisciplinary Sciences

Merging allylic carbon-hydrogen and selective carbon-carbon bond activation

Ahmad Masarwa et al.

NATURE (2014)

Review Chemistry, Multidisciplinary

C-C Fragmentation: Origins and Recent Applications

Michael A. Drahl et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Multidisciplinary

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

Christopher K. Prier et al.

CHEMICAL REVIEWS (2013)

Review Chemistry, Inorganic & Nuclear

Oxidative aliphatic carbon-carbon bond cleavage reactions

Caleb J. Allpress et al.

COORDINATION CHEMISTRY REVIEWS (2013)

Article Chemistry, Organic

Reaction products and mechanism of the regioselective oxidation of N-phenylmorpholine by ozone

Ricardo Suarez-Bertoa et al.

TETRAHEDRON (2012)

Review Chemistry, Multidisciplinary

Visible light photoredox catalysis: applications in organic synthesis

Jagan M. R. Narayanam et al.

CHEMICAL SOCIETY REVIEWS (2011)

Article Chemistry, Multidisciplinary

Visible light photocatalysis as a greener approach to photochemical synthesis

Tehshik P. Yoon et al.

NATURE CHEMISTRY (2010)

Review Chemistry, Multidisciplinary

Advances in the total synthesis of biologically important marine macrolides

KS Yeung et al.

CHEMICAL REVIEWS (2005)

Review Chemistry, Multidisciplinary

Total syntheses of marine polycyclic ethers

T Nakata

CHEMICAL REVIEWS (2005)

Article Plant Sciences

Bioactive tetrahydrofuran lignans from Peperomia dindygulensis

JL Wu et al.

JOURNAL OF NATURAL PRODUCTS (2005)