Hydrogen Bonding-Assisted and Nonheme Manganese-Catalyzed Remote Hydroxylation of C-H Bonds in Nitrogen-Containing Molecules

Article Chemistry, Multidisciplinary

Electrochemical Trifluoromethoxylation of (Hetero)aromatics with a Trifluoromethyl Source and Oxygen

Yao Ouyang et al.

Summary: The study introduces a novel electrochemical reaction method for the direct trifluoromethoxylation of aromatics, providing a valuable structural motif for drug discovery.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Physical

Theoretical Insight into the Mechanism and Selectivity in Manganese-Catalyzed Oxidative C(sp3)-H Methylation

Aili Feng et al.

Summary: Density functional theory calculations were used to investigate the mechanism and selectivity of the manganese-catalyzed oxidative C(sp(3))-H methylation reaction. The calculations revealed detailed mechanisms for the preactivation of the catalyst, formation of oxidant species, hydroxylation of the substrate, and methylation of the intermediate. The study identified key intermediates and active oxidants, and explained the alpha-site selectivity based on electronic effects.

ACS CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

Chemoselective Oxyfunctionalization of Functionalized Benzylic Compounds with a Manganese Catalyst

Jimei Zhou et al.

Summary: This study reports a new non-heme Mn catalyst that enables the benzylic oxidation reactions under mild conditions. The catalyst shows high activity and excellent selectivity, allowing for the oxidation of a wide range of functional groups. This method provides a cost-effective, sustainable, and robust pathway for the synthesis of ketones, increasing the complexity of organic molecules, and modifying drugs at a late stage.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Multidisciplinary

Resolving Oxygenation Pathways in Manganese-Catalyzed C(sp3)-H Functionalization via Radical and Cationic Intermediates

Marco Galeotti et al.

Summary: The C(sp(3))-H bond oxygenation of cyclopropane-containing mechanistic probes has been studied using hydrogen peroxide catalyzed by manganese complexes. The study showed the presence of both unrearranged and rearranged oxygenation products, suggesting the involvement of cationic intermediates and different pathways. The selective formation of either unrearranged or rearranged product in high yield can be achieved by choosing appropriate catalyst structure and reaction conditions.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Physical

Amine Organocatalysis of Remote, Chemoselective C(sp3)-H Hydroxylation

Philip L. Hahn et al.

Summary: In this study, an organocatalytic approach using secondary amines as catalysts foroxaziridinium-mediated C-H hydroxylation is introduced. The operationally simple catalytic strategy demonstrated advantages in achieving high yielding and highly selective remote hydroxylation of compounds with oxidation-sensitive functional groups. Hexafluoroisopropanol was used as the solvent in the absence of water, leading to a proposed hydrogen-bonding effect that resulted in high chemoselectivity for remote aliphatic hydroxylation of 2 degrees alcohols.

ACS CATALYSIS (2022)

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Article Chemistry, Physical

Bromoacetic Acid-Promoted Nonheme Manganese-CatalyzedAlkane Hydroxylation Inspired by?-Ketoglutarate-DependentOxygenases

Jie Chen et al.

Summary: Biomimetic iron and manganese complexes have been used as catalysts for selective oxidation reactions. In this study, a remote hydroxylation of undirected C(sp(3))-H bonds using a manganese catalyst and hydrogen peroxide as an oxidant was described. The catalytic system showed excellent activity, low catalyst loading, short reaction time, wide substrate scope, and easy scale-up. Mechanistic studies revealed the role of an additive in facilitating the generation of an electrophilic oxidant.

ACS CATALYSIS (2022)

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Article Chemistry, Organic

Manganese-Catalyzed Regioselective C-H Lactonization and Hydroxylation of Fatty Acids with H2O2

Vladimir I. Kurganskiy et al.

Summary: In this paper, the direct selective C-H lactonization of fatty acids (C5-C16) catalyzed by manganese(II) complexes bearing bis-amino-bis-pyridine ligands was reported. The catalyst system used environmentally benign hydrogen peroxide as an oxidant and showed high efficiency, providing gamma-lactones in 60-90% yields under optimized conditions. Remarkably, by changing the reaction conditions, the oxidation of hexanoic acid could be diverted to the formation of delta-caprolactone in up to 67% yield. Furthermore, the possibility of obtaining (omega-1)-hydroxy derivatives from linear C7-C10 acids in up to 48% yields was demonstrated.

ORGANIC LETTERS (2022)

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Review Chemistry, Multidisciplinary

HFIP in Organic Synthesis

Hashim F. Motiwala et al.

Summary: HFIP is a polar solvent that is widely used in organic synthesis for stabilizing ionic species, transferring protons, and engaging in various intermolecular interactions.

CHEMICAL REVIEWS (2022)

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Article Chemistry, Organic

Metal-Catalyzed C-H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products

Victor C. S. Santana et al.

Summary: C-H bond oxidation is a powerful tool for introducing oxygen atoms into organic molecules and provides a new perspective on retrosynthetic disconnections. This review summarizes the application of five metal-catalyzed methodologies for C(sp(3))-H oxidation in the total synthesis of natural and unnatural products.

SYNTHESIS-STUTTGART (2022)

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Article Chemistry, Physical

Direct regio- and stereoselective mono- and polyoxyfunctionalization of estrone derivatives at C(sp3)-H bonds

Roman V. Ottenbacher et al.

Summary: Late-stage catalytic selective oxidative C-H functionalization of estrone and estradiol derivatives using bioinspired nonheme Mn complexes yields versatile products for further oxidative transformations to generate polyoxygenated metabolites.

JOURNAL OF CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

Carboxylic Acid Directed ?-Lactonization of Unactivated Primary C-H Bonds Catalyzed by Mn Complexes: Application to Stereoselective Natural Product Diversification

Arnau Call et al.

Summary: Reactions that allow selective functionalization of strong aliphatic C-H bonds have the potential to increase molecular complexity and expand chemical space. This study describes the catalytic site- and stereoselective gamma-lactonization of unactivated primary C-H bonds in carboxylic acid substrates using a chiral Mn catalyst. The reaction exhibits high site-selectivity and enables the oxidation of weaker secondary and tertiary C-H bonds. By manipulating the chirality of the catalyst, the reaction can achieve high diastereoselectivity in the lactonization of methyl groups in rigid cyclic and bicyclic carboxylic acids. The mechanistic analysis suggests that the reaction proceeds through a rebound type mechanism initiated by intramolecular 1,7-HAT.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Review Chemistry, Multidisciplinary

Electronic control over site-selectivity in hydrogen atom transfer (HAT) based C(sp3)-H functionalization promoted by electrophilic reagents

Marco Galeotti et al.

Summary: Direct functionalization of C(sp(3))-H bonds is a key focus in developing new synthetic methods. Among intermolecular C-H bond functionalization strategies, hydrogen atom transfer (HAT) methods using radical or radical-like reagents have gained increasing attention due to their ability to introduce a variety of atoms and groups in mild conditions. Selectivity control over aliphatic C-H bonds is crucial and factors influencing it have been discussed. This review article provides a detailed description of HAT reagents, associated mechanistic features, and selectivity patterns observed in the functionalization of increasingly complex substrates, based on an analysis of recent literature.

CHEMICAL SOCIETY REVIEWS (2022)

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Article Chemistry, Multidisciplinary

General Access to Modified α-Amino Acids by Bioinspired Stereoselective γ-C-H Bond Lactonization

Laia Vicens et al.

Summary: The use of bioinspired manganese catalysts and H2O2 under mild conditions allows for the efficient preparation of modified alpha-amino acids. This method demonstrates outstanding site-selectivity and diastereoselectivity, potentially serving as an alternative to established organometallic procedures.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Organic

Insight into the Selective Methylene Oxidation Catalyzed by Mn(CF3-PDP)(SbF6)2/H2O2/CH2ClCO2H) System: A DFT Mechanistic Study

Ruihua Zhao et al.

Summary: DFT study was used to investigate the methylene oxidation catalyzed by Mn. The active catalyst was characterized as [Mn](O)OAcCI, which oxidizes the methylene group to alcohol and then to a carbonyl group sequentially. This mechanism explains the observed site selectivity.

ORGANIC LETTERS (2021)

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Review Chemistry, Inorganic & Nuclear

Biomimetic metal-oxidant adducts as active oxidants in oxidation reactions

Mian Guo et al.

Summary: This review focuses on the synthesis, characterization, and reactivity studies of metal-oxidant adducts in heme and nonheme systems, discussing the mechanisms of the conversion of metal-oxidant adducts to high-valent metal-oxo species and comparing the reactivities of the two.

COORDINATION CHEMISTRY REVIEWS (2021)

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Article Chemistry, Physical

Mn aminopyridine oxidase mimics: Switching between biosynthetic-like and xenobiotic regioselectivity in C-H oxidation of (-)-ambroxide

Roman V. Ottenbacher et al.

Summary: The late-stage CAH oxofunctionalization of (-)-ambroxide with H2O2 in the presence of bioinspired honheme Mn complexes is reported. Adjusting the ligand architecture and absolute chirality, as well as tuning the reaction solvent, allows switching the catalysts' selectivity between biosynthetic-like and bioorthogonal modes, thus directing the reaction towards various oxidized metabolites of (-)-ambroxide.

JOURNAL OF CATALYSIS (2021)

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Article Chemistry, Organic

Recent Strategies in Non-Heme-Type Metal Complex-Catalyzed Site-, Chemo-, and Enantioselective C-H Oxygenations

Daiki Doiuchi et al.

Summary: This paper reviews recent developments in non-heme-type complex-catalyzed C-H oxidations over the last fourteen years, discussing the applications of site-selective, chemo-selective, diastereo-selective, and enantioselective transformations in C-H oxidations.

SYNTHESIS-STUTTGART (2021)

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Article Chemistry, Physical

H-Bonding Networks Dictate the Molecular Mechanism of H2O2 Activation by P450

Xuan Zhang et al.

Summary: Understanding the molecular basis of controlled H2O2 activation is crucial for peroxide-driven catalysis by metalloenzymes. This study demonstrates the significant influence of substrates and dual-functional small molecules (DFSM) on H2O2 activation, with hydrogen bonding networks playing key roles in dictating the process.

ACS CATALYSIS (2021)

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Review Chemistry, Physical

Inspiration from Nature: Influence of Engineered Ligand Scaffolds and Auxiliary Factors on the Reactivity of Biomimetic Oxidants

Gourab Mukherjee et al.

Summary: Enzymes are efficient catalysts in nature that achieve high stereo-, chemo-, and regioselectivity through substrate binding and positioning in the active site, as well as second-coordination sphere effects. Biomimetic model complexes with similar first-coordination sphere to enzymes have been developed, but sometimes show different reactivity patterns in solution and loss of selectivity. Large catalytic clusters with second-coordination sphere effects have been developed to understand functional differences between enzymes and biomimetic models, influencing spectroscopic features and reactivity patterns for high selectivity in chemical reactions. The biomimetic models show potential for future stereo- and chemoselective synthetic catalytic reactions in biotechnological and engineering applications.

ACS CATALYSIS (2021)

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Article Chemistry, Physical

Mechanistic Guidance Leads to Enhanced Site-Selectivity in C-H Oxidation Reactions Catalyzed by Ruthenium bis(Bipyridine) Complexes

Jeremy D. Griffin et al.

Summary: This study presents a straightforward C-H oxidation protocol using an acid-stable, bis(bipyridine)Ru catalyst. It reveals that electronic differences remote to the C-H functionalization site affect product selectivity, and the choice of reaction solvent also plays a role in determining site-selectivity. A statistical model is detailed to correlate product selectivity outcomes with computational parameters describing the relative electron-richness of C-H bonds.

ACS CATALYSIS (2021)

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Article Chemistry, Applied

Chemoselective Tertiary C-H Hydroxylation for Late-Stage Functionalization with Mn(PDP)/Chloroacetic Acid Catalysis

Rachel K. Chambers et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Review Chemistry, Multidisciplinary

Second-Coordination Sphere Effects on Selectivity and Specificity of Heme and Nonheme Iron Enzymes

Sam P. de Visser

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Article Chemistry, Multidisciplinary

Enantioselective C-H Lactonization of Unactivated Methylenes Directed by Carboxylic Acids

Marco Cianfanelli et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Physical

Site-Selective and Product Chemoselective Aliphatic C-H Bond Hydroxylation of Polyhydroxylated Substrates

Margarida Borrell et al.

ACS CATALYSIS (2020)

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Article Multidisciplinary Sciences

Late-stage oxidative C(sp3)-H methylation

Kaibo Feng et al.

NATURE (2020)

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Article Chemistry, Organic

Electrochemical Ruthenium-Catalyzed C-H Hydroxylation of Amine Derivatives in Aqueous Acid

Sophia G. Robinson et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Physical

Highly enantioselective undirected catalytic hydroxylation of benzylic CH2 groups with H2O2

Roman Ottenbacher et al.

JOURNAL OF CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed meta-C-H Allylation of Arenes: A Unique Combination of a Pyrimidine-Based Template and Hexafluoroisopropanol

Sukdev Bag et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Review Chemistry, Inorganic & Nuclear

Artificial nonheme iron and manganese oxygenases for enantioselective olefin epoxidation and alkane hydroxylation reactions

Jie Chen et al.

COORDINATION CHEMISTRY REVIEWS (2020)

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Article Chemistry, Physical

Rational Design of Bioinspired Catalysts for Selective Oxidations

Laia Vicens et al.

ACS CATALYSIS (2020)

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Article Chemistry, Organic

Catalytic Enantioselective Methylene C(sp3)-H Hydroxylation Using a Chiral Manganese Complex/Carboxylic Acid System

Qiangsheng Sun et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Multidisciplinary

Exploiting hexafluoroisopropanol (HFIP) in Lewis and Bronsted acid-catalyzed reactions

Valentyn Pozhydaiev et al.

CHEMICAL COMMUNICATIONS (2020)

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Review Chemistry, Multidisciplinary

Iron- and cobalt-catalyzed C(sp3)-H bond functionalization reactions and their application in organic synthesis

Yungen Liu et al.

CHEMICAL SOCIETY REVIEWS (2020)

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Review Chemistry, Multidisciplinary

Bioinspired Manganese and Iron Complexes for Enantioselective Oxidation Reactions: Ligand Design, Catalytic Activity, and Beyond

Wei Sun et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

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Article Chemistry, Inorganic & Nuclear

High-Spin Mn(V)-Oxo Intermediate in Nonheme Manganese Complex-Catalyzed Alkane Hydroxylation Reaction: Experimental and Theoretical Approach

Xiao-Xi Li et al.

INORGANIC CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Mechanistic Study of Ruthenium-Catalyzed C-H Hydroxylation Reveals an Unexpected Pathway for Catalyst Arrest

James B. C. Mack et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Multidisciplinary

Chemoselective methylene oxidation in aromatic molecules

Jinpeng Zhao et al.

NATURE CHEMISTRY (2019)

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Review Chemistry, Multidisciplinary

Role of hexafluoroisopropanol in C-H activation

Soumya Kumar Sinha et al.

REACTION CHEMISTRY & ENGINEERING (2019)

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Review Chemistry, Multidisciplinary

Activation and Deactivation Strategies Promoted by Medium Effects for Selective Aliphatic C-H Bond Functionalization

Massimo Bietti

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Article Chemistry, Multidisciplinary

Organic synthesis provides opportunities to transform drug discovery

David C. Blakemore et al.

NATURE CHEMISTRY (2018)

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Article Chemistry, Physical

Mechanistic Insights into the Enantioselective Epoxidation of Olefins by Bioinspired Manganese Complexes: Role of Carboxylic Acid and Nature of Active Oxidant

Junyi Du et al.

ACS CATALYSIS (2018)

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Review Chemistry, Multidisciplinary

The Quest for Selectivity in Hydrogen Atom Transfer Based Aliphatic C-H Bond Oxygenation

Michela Milan et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

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Review Chemistry, Multidisciplinary

Aliphatic C-H Oxidations for Late-Stage Functionalization

M. Christina White et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Physical

Enantioselective Benzylic Hydroxylation of Arylalkanes with H2O2 in Fluorinated Alcohols in the Presence of Chiral Mn Aminopyridine Complexes

Roman V. Ottenbacher et al.

CHEMCATCHEM (2018)

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Article Chemistry, Multidisciplinary

Ruthenium-Catalyzed C-H Hydroxylation in Aqueous Acid Enables Selective Functionalization of Amine Derivatives

James B. C. Mack et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Article Chemistry, Organic

Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate

Melissa Lee et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Multidisciplinary

Chemoselective Aliphatic C-H Bond Oxidation Enabled by Polarity Reversal

Valeria Dantignana et al.

ACS CENTRAL SCIENCE (2017)

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Review Chemistry, Multidisciplinary

Hexafluoroisopropanol as a highly versatile solvent

Ignacio Colomer et al.

NATURE REVIEWS CHEMISTRY (2017)

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Oxyfunctionalization of the Remote C-H Bonds of Aliphatic Amines by Decatungstate Photocatalysis

Danielle M. Schultz et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Multidisciplinary

Remote meta-C-H Cyanation of Arenes Enabled by a Pyrimidine-Based Auxiliary

Sukdev Bag et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Multidisciplinary

Selective Aerobic Oxidation of Methylarenes to Benzaldehydes Catalyzed by N-Hydroxyphthalimide and Cobalt(II) Acetate in Hexafluoropropan-2-ol

Eden Gaster et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Multidisciplinary

Synthesis of Active Hexafluoroisopropyl Benzoates through a Hydrogen-Bond-Enabled Palladium(II)-Catalyzed C-H Alkoxycarbonylation Reaction

Yang Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Multidisciplinary

Hydrogen Bonding to Hexafluoroisopropanol Controls the Oxidative Strength of Hypervalent Iodine Reagents

Ignacio Colomer et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Chemistry, Multidisciplinary

Mononuclear Nonheme High-Spin Iron(III)-Acylperoxo Complexes in Olefin Epoxidation and Alkane Hydroxylation Reactions

Bin Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Multidisciplinary Sciences

Oxidative diversification of amino acids and peptides by small-molecule iron catalysis

Thomas J. Osberger et al.

NATURE (2016)

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Article Chemistry, Organic

Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C-H Sites

Curren T. Mbofana et al.

ORGANIC LETTERS (2016)

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An Iminium Salt Organocatalyst for Selective Aliphatic C-H Hydroxylation

Daoyong Wang et al.

ORGANIC LETTERS (2016)

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Review Chemistry, Multidisciplinary

Molecular Designs for Controlling the Local Environments around Metal Ions

Sarah A. Cook et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

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Review Chemistry, Multidisciplinary

Tuning Reactivity and Selectivity in Hydrogen Atom Transfer from Aliphatic C-H Bonds to Alkoxyl Radicals: Role of Structural and Medium Effects

Michela Salamone et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

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Article Chemistry, Multidisciplinary

Platinum-Catalyzed, Terminal-Selective C(sp3)-H Oxidation of Aliphatic Amines

Melissa Lee et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Multidisciplinary

Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules

Jennifer M. Howell et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Multidisciplinary

Trapping a Highly Reactive Nonheme Iron Intermediate That Oxygenates Strong C-H Bonds with Stereoretention

Joan Serrano-Plana et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Organic

Comparative Study of the Limitations and Challenges in Atom-Transfer C-H Oxidations

Ashley M. Adams et al.

ORGANIC LETTERS (2015)

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Article Chemistry, Medicinal

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals

Edon Vitaku et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

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Article Chemistry, Multidisciplinary

Non-directed allylic C-H acetoxylation in the presence of Lewis basic heterocycles

Hasnain A. Malik et al.

CHEMICAL SCIENCE (2014)

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Identification of a low-spin acylperoxoiron(III) intermediate in bio-inspired non-heme iron-catalysed oxidations

Williamson N. Oloo et al.

NATURE COMMUNICATIONS (2014)

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Article Chemistry, Physical

Nonheme Iron Oxidant Formed in the Presence of H2O2 and Acetic Acid Is the Cyclic Ferric Peracetate Complex, Not a Perferryloxo Complex

Yong Wang et al.

ACS CATALYSIS (2013)

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Oxadiazoles in Medicinal Chemistry

Jonas Bostrom et al.

JOURNAL OF MEDICINAL CHEMISTRY (2012)

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Editorial Material Multidisciplinary Sciences

Adding Aliphatic C-H Bond Oxidations to Synthesis

M. Christina White

SCIENCE (2012)

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Hydrocarbon Hydroxylation by Cytochrome P450 Enzymes

Paul R. Ortiz de Montellano

CHEMICAL REVIEWS (2010)

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Role of the Secondary Coordination Sphere in Metal-Mediated Dioxygen Activation

Ryan L. Shook et al.

INORGANIC CHEMISTRY (2010)

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The effects of hydrogen bonds on metal-mediated O-2 activation and related processes

Ryan L. Shook et al.

CHEMICAL COMMUNICATIONS (2008)

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Bioinspired hydrogen bond motifs in ligand design: The role of noncovalent interactions in metal ion mediated activation of dioxygen

AS Borovik

ACCOUNTS OF CHEMICAL RESEARCH (2005)

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Dioxygen activation at mononuclear nonheme iron active sites: Enzymes, models, and intermediates

M Costas et al.

CHEMICAL REVIEWS (2004)

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Hydrogen Bonding-Assisted and Nonheme Manganese-Catalyzed Remote Hydroxylation of C-H Bonds in Nitrogen-Containing Molecules

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