☆ 4.8 Review

Transition-Metal-Catalyzed C-H Bond Activation for the Formation of C-C Bonds in Complex Molecules

CHEMICAL REVIEWS (2023)

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Summary: Bioorthogonal diversification of peptides usually relies on impractical prefunctionalization methods. The authors have developed a manganese(I)-catalyzed C-H fluorescent labeling with BODIPY probes, which enables the development of activatable fluorophores for imaging cell function.

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Summary: The utilization of natural Asp as a directing group in the late-stage C(sp(3))-H arylation and alkynylation of peptide sequences containing L- and D-alanines has enabled the access to peptide sequences containing unnatural amino acids. With this method, 60 modified peptides were obtained in moderate to excellent yields under mild conditions, allowing for the construction of strongly fluorescent BODIPY-labeled peptides.

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Late-stage C-H functionalization offers new opportunities in drug discovery

Lucas Guillemard et al.

Summary: In the past decade, the introduction of late-stage functionalization methodologies has significantly advanced the landscape of molecular synthesis. Particularly, C-H functionalization approaches have led to improvements in resource economy and new strategies for drug discovery. However, challenges and limitations in current LSF methods indicate the need for future improvements and development of new approaches.

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The emergence of the C-H functionalization strategy in medicinal chemistry and drug discovery

Ranjan Jana et al.

Summary: Due to market competition and societal demand, the speed of drug discovery is crucial for successful implementation. C-H activation technology allows for rapid construction and modification of functional molecules, expanding chemical space and offering immense potential for rapid synthesis and structural modification of drug molecules.

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DNA-Encoded Chemical Libraries: A Comprehensive Review with Succesful Stories and Future Challenges

Adrian Gironda-Martinez et al.

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Ru-catalyzed room-temperature alkylation and late-stage alkylation of arenes with primary alkyl bromides

Matthew Wheatley et al.

Summary: A cyclometallated Ru complex has been developed for the C-H alkylation of arenes with various N-based directing groups using primary alkyl bromides at room temperature. The method shows great promise for late-stage functionalization, with mechanistic studies revealing a bis-cyclometallated Ru intermediate and an SN2-type oxidative addition pathway.

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Highly regioselective and stereoselective synthesis of C-Aryl glycosides via nickel-catalyzed ortho-C-H glycosylation of 8-aminoquinoline benzamides

Wei-Yu Shi et al.

Summary: A novel and cost-effective nickel-catalyzed ortho-C-Ar-H glycosylation reaction with high regioselectivity and excellent alpha-selectivity is described in this study. The method shows great functional group compatibility with various glycosides, demonstrating its synthetic potential. Mechanistic studies suggest that C-H activation could be the rate-determining step.

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Installing the magic methyl - C-H methylation in synthesis

Daniya Aynetdinova et al.

Summary: This review discusses diverse techniques for selectively installing the C-Me bond in a wide range of chemical structures, from simple building blocks to complex drug-like architectures.

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Palladium-Catalyzed Regioselective Arylation of Unprotected Allylamines

Vinod G. Landge et al.

Summary: The translation discusses the challenges of palladium-catalyzed organometallic transformations of free amines and the importance of accessing free amine products. It also highlights the significance of the 3,3-diarylallylamine motif and the development of a catalytic approach for their synthesis. The method allows for mild conditions, broad substrate scope, and direct diarylation of terminal allylamine substrates.

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Metal-catalyzed silylation of sp3C-H bonds

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Summary: Metal-catalyzed silylation reactions play a crucial role in the synthesis of organometallic compounds, especially in the activation of sp(3)C-H bonds. By utilizing different metal catalysts, intermolecular and intramolecular sp(3)C-H bond silylations directed by nitrogen-containing heterocycles or amide functions can be achieved for the formation of stable organometallic species.

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Jeroen B. I. Sap et al.

Summary: This review discusses recent advances in difluoromethylation processes, focusing on X-CF2H bond formation and the development of various difluoromethylation reagents. Metal-based methods have shown promise in transferring CF2H to C(sp(2)) sites, while Minisci-type radical chemistry has been successfully applied to difluoromethylate C(sp(2))-H bonds.

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Deaminative meta-C-H alkylation by ruthenium(ii) catalysis

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Summary: The study reported a ruthenium-catalyzed meta-C-H deaminative alkylation using easily accessible amino acid-derived Katritzky pyridinium salts, as well as remote C-H benzylations with high levels of chemoselectivity and remarkable functional group tolerance. This method, combining meta-C-H activation with deaminative strategy, represents a rare example of selectively converting C(sp(3))-N bonds into C(sp(3))-C(sp(2)) bonds.

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Matthias R. Bauer et al.

Summary: This review discusses the increasing use of aliphatic three- and four-membered rings in medicinal chemistry, highlighting both their advantages and potential risks. Understanding the characteristics of small ring structures is crucial for enhancing the efficacy and safety of pharmaceuticals.

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Catalytic C-H to C-M (M = Al, Mg) bond transformations with heterometallic complexes

Maria Batuecas et al.

Summary: This passage discusses the importance of C-H functionalization, particularly the fast-developing field of C-H borylation. It focuses on palladium- and calcium-catalyzed methods for C-H metalation, revealing new reaction pathways and mechanisms.

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Catalysis using transition metal complexes featuring main group metal and metalloid compounds as supporting ligands

Jun Takaya

Summary: Recent research has demonstrated the promising utility of transition metal complexes with M-E bonds stabilized by multidentate ligands, where E represents a main group metal or metalloid element. Main group metal and metalloid ligands provide unique electronic and steric environments to transition metals, leading to remarkable catalytic activity and product selectivity. This perspective highlights the potential of these compounds as a new class of supporting ligands for transition metal catalysts in synthetic chemistry.

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One-Pot Approach to 8-Acylated 2-Quinolinones via Palladium-Catalyzed Regioselective Acylation of Quinoline N-Oxides

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Article Multidisciplinary Sciences

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β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp3)-H bonds using a palladium catalyst

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Functionalized Polymer-Supported Pyridine Ligands for Palladium-Catalyzed C(sp3)-H Arylation

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Review Chemistry, Physical

Regioselectivity in palladium-catalysed direct arylation of 5-membered ring heteroaromatics

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Pd(II)-catalyzed beta-C-H arylation of O-methyl ketoximes with iodoarenes

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Undirected, Homogeneous C-H Bond Functionalization: Challenges and Opportunities

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Enabling Technologies for the Future of Chemical Synthesis

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The Chemical Space Project

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ACCOUNTS OF CHEMICAL RESEARCH (2015)

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Review Chemistry, Multidisciplinary

Catalytic Silylation of Unactivated C-H Bonds

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Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C-H Activation Reactions

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CHEMISTRY LETTERS (2015)

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Late-Stage Peptide Diversification by Bioorthogonal Catalytic CH Arylation at 23°C in H2O

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Iridium(III)-Catalyzed Direct Arylation of C-H Bonds with Diaryliodonium Salts

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Editorial Material Multidisciplinary Sciences

Why synthesize?

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An analysis of the attrition of drug candidates from four major pharmaceutical companies

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Current complexity: a tool for assessing the complexity of organic molecules

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Introduction of Hindered Electrophiles via C-H Functionalization in a Palladium-Catalyzed Multicomponent Domino Reaction

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New peptide architectures through C-H activation stapling between tryptophan-phenylalanine/tyrosine residues

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NATURE COMMUNICATIONS (2015)

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Weakly Coordinating Directing Groups for Ruthenium(II)-Catalyzed C-H Activation

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ADVANCED SYNTHESIS & CATALYSIS (2014)

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C-H Functionalization in the Synthesis of Amino Acids and Peptides

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CHEMICAL REVIEWS (2014)

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Late-Stage Diversification of Peptides by Metal-Free C-H Arylation

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Targeting the Androgen Receptor with Steroid Conjugates

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Rings in Drugs

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JOURNAL OF MEDICINAL CHEMISTRY (2014)

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Beyond Classical Reactivity Patterns: Hydroformylation of Vinyl and Allyl Arenes to Valuable β- and γ-Aldehyde Intermediates Using Supramolecular Catalysis

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Role of Sterically Demanding Chiral Dirhodium Catalysts in Site-Selective C-H Functionalization of Activated Primary C-H Bonds

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Site-Selective C(sp3)-H Functionalization of Di-, Tr-, and Tetrapeptides at the N-Terminus

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Regioselective Introduction of Heteroatoms at the C-8 Position of Quinoline N-Oxides: Remote C-H Activation Using N-Oxide as a Stepping Stone

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Chemistry, Organic

Cobalt-Catalyzed Hydroarylative Cyclization of 1,6-Enynes with Aromatic Ketones and Esters via C-H Activation

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ORGANIC LETTERS (2014)

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Article Multidisciplinary Sciences

Organic synthesis: the art and science of replicating the molecules of living nature and creating others like them in the laboratory

K. C. Nicolaou

PROCEEDINGS OF THE ROYAL SOCIETY A-MATHEMATICAL PHYSICAL AND ENGINEERING SCIENCES (2014)

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Threefold Cross-Linked Polystyrene-Triphenylphosphane Hybrids: Mono-P-Ligating Behavior and Catalytic Applications for Aryl Chloride Cross-Coupling and C(sp3)-H Borylation

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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C-H Functionalization Logic Enables Synthesis of (+)-Hongoquercin A and Related Compounds

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Profound Methyl Effects in Drug Discovery and a Call for New C-H Methylation Reactions

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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A Cationic High-Valent Cp*CoIII Complex for the Catalytic Generation of Nucleophilic Organometallic Species: Directed C-H Bond Activation

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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On Water, Phosphine-Free Palladium-Catalyzed Room Temperature C-H Arylation of Indoles

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CHEMISTRY-A EUROPEAN JOURNAL (2013)

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Meta-Selective C-H Functionalization Using a Nitrile-Based Directing Group and Cleavable Si-Tether

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meta-Selective C-H Bond Alkylation with Secondary Alkyl Halides

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

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Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate

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A robustness screen for the rapid assessment of chemical reactions

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NATURE CHEMISTRY (2013)

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Silica-Immobilized Chiral Dirhodium(II) Catalyst for Enantioselective Carbenoid Reactions

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ORGANIC LETTERS (2013)

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Review Chemistry, Multidisciplinary

Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions

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ACCOUNTS OF CHEMICAL RESEARCH (2012)

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C-H Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

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Review Biochemical Research Methods

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Peptidic macrocyclization via palladium-catalyzed chemoselective indole C-2 arylation

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CHEMICAL COMMUNICATIONS (2012)

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Dehydrative C-H Alkylation and Alkenylation of Phenols with Alcohols: Expedient Synthesis for Substituted Phenols and Benzofurans

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

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Catalytic Functionalization of Unactivated sp3 C-H Bonds via exo-Directing Groups: Synthesis of Chemically Differentiated 1,2-Diols

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Activation of remote meta-C-H bonds assisted by an end-on template

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NATURE (2012)

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Metal-Free N-H Insertions of Donor/Acceptor Carbenes

Stephanie R. Hansen et al.

ORGANIC LETTERS (2012)

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Ruthenium-Catalyzed C-H Bond Arylations of Arenes Bearing Removable Directing Groups via Six-Membered Ruthenacycles

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ORGANIC LETTERS (2012)

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Oxidizing Directing Groups Enable Efficient and Innovative C-H Activation Reactions

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

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Palladium-Catalyzed Borylation of Sterically Demanding Aryl Halides with a Silica-Supported Compact Phosphane Ligand

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

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One-Step Catalytic Asymmetric Synthesis of Configurationally Stable Troger Bases

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

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Review Chemistry, Organic

1,2,3-Triazoles in Peptidomimetic Chemistry

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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2011)

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Ruthenium-Catalyzed Meta Sulfonation of 2-Phenylpyridines

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

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Divergent C-H Functionalizations Directed by Sulfonamide Pharmacophores: Late-Stage Diversification as a Tool for Drug Discovery

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

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Carboxylate-Assisted Ruthenium-Catalyzed Direct Alkylations of Ketimines

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ORGANIC LETTERS (2011)

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Selective Catalytic C-H Alkylation of Alkenes with Alcohols

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SCIENCE (2011)

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Review Chemistry, Applied

Regioselective Functionalization of the Imidazole Ring via Transition Metal-Catalyzed C-N and C-C Bond Forming Reactions

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ADVANCED SYNTHESIS & CATALYSIS (2010)

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1,7-Disubstituted oxyindoles are potent and selective EP3 receptor antagonists

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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2010)

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Postsynthetic Modification of Peptides: Chemoselective C-Arylation of Tryptophan Residues

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CHEMISTRY-A EUROPEAN JOURNAL (2010)

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Enantioselective Ring Opening of Epoxides by Fluoride Anion Promoted by a Cooperative Dual-Catalyst System

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[Ir(COD)Cl]2 as a Catalyst Precursor for the Intramolecular Hydroamination of Unactivated Alkenes with Primary Amines and Secondary Alkyl- or Arylamines: A Combined Catalytic, Mechanistic, and Computational Investigation

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Pd(II)-Catalyzed Carbonylation of C(sp3)-H Bonds: A New Entry to 1,4-Dicarbonyl Compounds

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Intermolecular Dehydrative Coupling Reaction of Aryl Ketones with Cyclic Alkenes Catalyzed by a Well-Defined Cationic Ruthenium-Hydride Complex: A Novel Ketone Olefination Method via Vinyl C-H Bond Activation

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ORGANOMETALLICS (2010)

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Article Chemistry, Multidisciplinary

Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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Article Biochemistry & Molecular Biology

Fluorinated isatin derivatives. Part 1: Synthesis of new N-substituted (S)-5-[1-(2-methoxymethylpyrrolidinyl) sulfonyl]isatins as potent caspase-3 and-7 inhibitors

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BIOORGANIC & MEDICINAL CHEMISTRY (2009)

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Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success

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JOURNAL OF MEDICINAL CHEMISTRY (2009)

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Article Chemistry, Organic

Regioselective Ruthenium-Catalyzed Direct Benzylations of Arenes through C-H Bond Cleavages

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ORGANIC LETTERS (2009)

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Article Chemistry, Inorganic & Nuclear

Regioselective Intermolecular Coupling Reaction of Arylketones and Alkenes Involving C-H Bond Activation Catalyzed by an in Situ Formed Cationic Ruthenium Hydride Complex

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ORGANOMETALLICS (2009)

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Total Synthesis of (+)-11,11′-Dideoxyverticillin A

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SCIENCE (2009)

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Estimation of synthetic accessibility score of drug-like molecules based on molecular complexity and fragment contributions

Peter Ertl et al.

JOURNAL OF CHEMINFORMATICS (2009)

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Pd(II)-catalyzed cross-coupling of sp3 C-H bonds with sp2 and sp3 boronic acids using air as the oxidant

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Asymmetric intramolecular arylcyanation of unactivated Olefins via C-CN bond activation

Mary P. Watson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Total Syntheses of (±)-Massadine and Massadine Chloride

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Article Chemistry, Multidisciplinary

Room temperature and phosphine free palladium catalyzed direct C-2 arylation of indoles

Nathalie Lebrasseur et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Synthesis of 1,2-and 1,3-Dicarboxylic Acids via Pd(II)-Catalyzed Carboxylation of Aryl and Vinyl C-H Bonds

Ramesh Giri et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Article Chemistry, Multidisciplinary

Palladium-catalyzed methylation and arylation of sp2 and sp3 C-H bonds in simple carboxylic acids

Ramesh Giri et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Review Chemistry, Multidisciplinary

Multisubstituted olefins: Platform synthesis and applications to materials science and pharmaceutical chemistry

Kenichiro Itami et al.

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2006)

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Review Biochemical Research Methods

Computational methods in developing quantitative structure-activity relationships (QSAR):: A review

AZ Dudek et al.

COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING (2006)

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Review Chemistry, Organic

Recent advances in the Stevens rearrangement of ammonium ylides. Application to the synthesis of alkaloid natural products

JA Vanecko et al.

TETRAHEDRON (2006)

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Green solvents for sustainable organic synthesis: state of the art

RA Sheldon

GREEN CHEMISTRY (2005)

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Review Chemistry, Multidisciplinary

Atroposelective synthesis of axially chiral biaryl compounds

G Bringmann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

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