Recent Advances on Amino Acid Modifications via C-H Functionalization and Decarboxylative Functionalization Strategies

Merging Photoredox with Copper Catalysis: Decarboxylative Alkynylation of α-Amino Acid Derivatives

(2017) Hao Zhang et al.   ORGANIC LETTERS

Highly Efficient and Divergent Construction of Chiral γ-Phosphono-α-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated C(sp3)–H Bonds

(2017) Qiang Yang et al.   ACS Catalysis

Homochirality of β-Peptides: A Significant Biomimetic Property of Unnatural Systems

(2017) István M. Mándity et al.   ChemistryOpen

Accelerated Synthesis of Protected Peptides in a Continuous-Flow Fixed-Bed Reactor

(2017) Aliz Szloszár et al.   ChemistrySelect

Syntheses and Transformations of α-Amino Acids via Palladium-Catalyzed Auxiliary-Directed sp3 C–H Functionalization

(2016) Gang He et al.   ACCOUNTS OF CHEMICAL RESEARCH

Ligand-Enabled Arylation of γ-C−H Bonds

(2016) Suhua Li et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)–H bonds at room temperature

(2016) Xinglin Yang et al.   CHEMICAL COMMUNICATIONS

Gold-Catalyzed Cycloisomerization of Alkyne-Containing Amino Acids: Controlled Tuning of C-N vs. C-O Reactivity

(2016) Noelia S. Medran et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Nickel-Catalyzed ortho-C-H Thiolation of N-Benzoyl α-Amino Acid Derivatives

(2016) Feng Gao et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of 1,3-Disubstituted Imidazo[1,5-a]pyridines from Amino Acids via Catalytic Decarboxylative Intramolecular Cyclization

(2016) Huiqiao Wang et al.   JOURNAL OF ORGANIC CHEMISTRY

Palladium-Catalyzed Ortho-Alkoxylation of N-Benzoyl α-Amino Acid Derivatives at Room Temperature

(2016) Shuangjie Li et al.   JOURNAL OF ORGANIC CHEMISTRY

Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis

(2016) Zhiwei Zuo et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Palladium-catalyzed β-C(sp3)–H arylation of phthaloyl alanine with hindered aryl iodides: synthesis of complex β-aryl α-amino acids

(2016) Xuekai Zhang et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Unprotected Amino Acids as Stable Radical Precursors for Heterocycle C–H Functionalization

(2016) Duy N. Mai et al.   ORGANIC LETTERS

Decarboxylative Annulation of α-Amino Acids with γ-Nitroaldehydes

(2016) YoungKu Kang et al.   ORGANIC LETTERS

Direct, visible light-sensitized benzylic C H fluorination of peptides using dibenzosuberenone: selectivity for phenylalanine-like residues

(2016) Desta Doro Bume et al.   TETRAHEDRON

Stereoselective alkoxycarbonylation of unactivated C(sp3)–H bonds with alkyl chloroformates via Pd(II)/Pd(IV) catalysis

(2016) Gang Liao et al.   Nature Communications

Photoredox/Brønsted Acid Co-Catalysis Enabling Decarboxylative Coupling of Amino Acid and Peptide Redox-Active Esters with N-Heteroarenes

(2016) Wan-Min Cheng et al.   ACS Catalysis

Room-Temperature Decarboxylative Alkynylation of Carboxylic Acids Using Photoredox Catalysis and EBX Reagents

(2015) Franck Le Vaillant et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Visible-Light-Induced Decarboxylative Functionalization of Carboxylic Acids and Their Derivatives

(2015) Jun Xuan et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Understanding the Effects of Bidentate Directing Groups: A Unified Rationale for sp2 and sp3 C–H Bond Activations

(2015) Hao Tang et al.   JOURNAL OF ORGANIC CHEMISTRY

Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides

(2015) Adam Noble et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Ligand-Enabled β-C–H Arylation of α-Amino Acids Using a Simple and Practical Auxiliary

(2015) Gang Chen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Ligand-Enabled Stereoselective β-C(sp3)–H Fluorination: Synthesis of Unnatural Enantiopure anti-β-Fluoro-α-amino Acids

(2015) Ru-Yi Zhu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Stereoselective Synthesis of Chiral β-Fluoro α-Amino Acids via Pd(II)-Catalyzed Fluorination of Unactivated Methylene C(sp3)–H Bonds: Scope and Mechanistic Studies

(2015) Qi Zhang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

One-Pot Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives via a Copper-Catalyzed Aerobic Oxidative Domino Reaction

(2015) Huanhuan Liu et al.   ORGANIC LETTERS

Benzoic Acid Catalyzed Annulations of α-Amino Acids and Aromatic Aldehydes Containing an ortho-Michael Acceptor: Access to 2,5-Dihydro-1H-benzo[c]azepines and 10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a]azepines

(2015) Mi Tang et al.   ORGANIC LETTERS

Molecular Iodine-Mediated Chemoselective Synthesis of Multisubstituted Pyridines through Catabolism and Reconstruction Behavior of Natural Amino Acids

(2015) Jia-Chen Xiang et al.   ORGANIC LETTERS

Cobalt-Catalyzed Decarboxylative Acetoxylation of Amino Acids and Arylacetic Acids

(2015) Kun Xu et al.   ORGANIC LETTERS

Auxiliary-Directed Pd-Catalyzed γ-C(sp3)–H Bond Activation of α-Aminobutanoic Acid Derivatives

(2015) Kalyan Kumar Pasunooti et al.   ORGANIC LETTERS

Palladium-Catalyzed Site-Selective Fluorination of Unactivated C(sp3)–H Bonds

(2015) Jinmin Miao et al.   ORGANIC LETTERS

Visible Light Catalysis Assisted Site-Specific Functionalization of Amino Acid Derivatives by C–H Bond Activation without Oxidant: Cross-Coupling Hydrogen Evolution Reaction

(2015) Xue-Wang Gao et al.   ACS Catalysis

Palladium-catalyzed alkylation of unactivated C(sp3)–H bonds with primary alkyl iodides at room temperature: facile synthesis of β-alkyl α-amino acids

(2015) B. Wang et al.   Organic Chemistry Frontiers

Sulfonamide-Promoted Palladium(II)-Catalyzed Alkylation of Unactivated Methylene C(sp3)H Bonds with Alkyl Iodides

(2014) Kai Chen et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Direct Borylation of Primary CH Bonds in Functionalized Molecules by Palladium Catalysis

(2014) Li-Sheng Zhang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

A mild and selective Pd-mediated methodology for the synthesis of highly fluorescent 2-arylated tryptophans and tryptophan-containing peptides: a catalytic role for Pd0 nanoparticles?

(2014) Thomas J. Williams et al.   CHEMICAL COMMUNICATIONS

A general and practical palladium-catalyzed monoarylation of β-methyl C(sp3)–H of alanine

(2014) Kai Chen et al.   CHEMICAL COMMUNICATIONS

n-Bu4NI-catalyzed selective dual amination of sp3 C–H bonds: oxidative domino synthesis of imidazo[1,5-c]quinazolines on a gram-scale

(2014) Dan Zhao et al.   CHEMICAL COMMUNICATIONS

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

(2014) Anaïs F. M. Noisier et al.   CHEMICAL REVIEWS

Exploiting Aromatic Interactions for β-Peptide Foldamer Helix Stabilization: A Significant Design Element

(2014) István M. Mándity et al.   CHEMISTRY-A EUROPEAN JOURNAL

Bio-Based Nitriles from the Heterogeneously Catalyzed Oxidative Decarboxylation of Amino Acids

(2014) Laurens Claes et al.   ChemSusChem

Continuous-Flow Solid-Phase Peptide Synthesis: A Revolutionary Reduction of the Amino Acid Excess

(2014) István M. Mándity et al.   ChemSusChem

Decarboxylative Arylation of α-Amino Acids via Photoredox Catalysis: A One-Step Conversion of Biomass to Drug Pharmacophore

(2014) Zhiwei Zuo et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines

(2014) Adam Noble et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Ligand-Promoted Alkylation of C(sp3)–H and C(sp2)–H Bonds

(2014) Ru-Yi Zhu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Palladium-Catalyzed Stereoretentive Olefination of Unactivated C(sp3)–H Bonds with Vinyl Iodides at Room Temperature: Synthesis of β-Vinyl α-Amino Acids

(2014) Bo Wang et al.   ORGANIC LETTERS

Total Synthesis of Hibispeptin A via Pd-Catalyzed C(sp3)–H Arylation with Sterically Hindered Aryl Iodides

(2014) Gang He et al.   ORGANIC LETTERS

Merging photoredox with nickel catalysis: Coupling of  -carboxyl sp3-carbons with aryl halides

(2014) Z. Zuo et al.   SCIENCE

Facile one-pot synthesis of tetrahydroisoquinolines from amino acids via hypochlorite-mediated decarboxylation and Pictet–Spengler condensation

(2014) Justin J. Maresh et al.   TETRAHEDRON LETTERS

Palladium-catalyzed trifluoroacetate-promoted mono-arylation of the β-methyl group of alanine at room temperature: synthesis of β-arylated α-amino acids through sequential C–H functionalization

(2014) Bo Wang et al.   Chemical Science

Stereoselective Synthesis of Chiral α-Amino-β-Lactams through Palladium(II)-Catalyzed Sequential Monoarylation/Amidation of C(sp3)H Bonds

(2013) Qi Zhang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Palladium-Catalyzed Direct Functionalization of 2-Aminobutanoic Acid Derivatives: Application of a Convenient and Versatile Auxiliary

(2013) Mengyang Fan et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Deaminative and Decarboxylative Catalytic Alkylation of Amino Acids with Ketones

(2013) Nishantha Kalutharage et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated γ C(sp3)H Bonds

(2013) Gang He et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Novel preparation of chiral α-amino acids using the Mitsunobu–Tsunoda reaction

(2013) Anaïs F. M. Noisier et al.   CHEMICAL COMMUNICATIONS

Future directions for peptide therapeutics development

(2013) Allan A. Kaspar et al.   DRUG DISCOVERY TODAY

Direct Synthesis of 2,5-Disubstituted Oxazoles through an Iodine-Catalyzed Decarboxylative Domino Reaction

(2013) Wei Xu et al.   JOURNAL OF ORGANIC CHEMISTRY

Palladium-Catalyzed Regioselective C-5 Arylation of Protected l-Histidine: Microwave-Assisted C–H Activation Adjacent to Donor Arm

(2013) Amit Mahindra et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of C-2 Arylated Tryptophan Amino Acids and Related Compounds through Palladium-Catalyzed C–H Activation

(2013) Sara Preciado et al.   JOURNAL OF ORGANIC CHEMISTRY

Palladium-Catalyzed Picolinamide-Directed Alkylation of Unactivated C(sp3)–H Bonds with Alkyl Iodides

(2013) Shu-Yu Zhang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Stereoselective Synthesis of β-Alkylated α-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated Methylene C(sp3)–H Bonds with Primary Alkyl Halides

(2013) Shu-Yu Zhang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Stereocontrolled synthesis of five diastereomers of trimethyl 3-aminocyclopentane-1,2,4-tricarboxylates

(2013) Ferenc Miklós et al.   TETRAHEDRON LETTERS

1,2,3-Triazoles as versatile directing group for selective sp2 and sp3 C–H activation: cyclization vs substitution

(2013) Xiaohan Ye et al.   Chemical Science

Controlling Site Selectivity in Palladium-Catalyzed C–H Bond Functionalization

(2012) Sharon R. Neufeldt et al.   ACCOUNTS OF CHEMICAL RESEARCH

Synthesis of Aromatic α-Aminoesters: Palladium-Catalyzed Long-Range Arylation of Primary C sp 3H Bonds

(2012) Sam Aspin et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nonnatural Amino Acid Synthesis by Using Carbon-Hydrogen Bond Functionalization Methodology

(2012) Ly Dieu Tran et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Biomedical applications of amino acid-modified chitosans: A review

(2012) Luca Casettari et al.   BIOMATERIALS

The Future of Peptide-based Drugs

(2012) David J. Craik et al.   Chemical Biology & Drug Design

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

(2012) Huijun Dong et al.   CHEMICAL COMMUNICATIONS

Highly Efficient 1,4-Addition of Aldehydes to Nitroolefins: Organocatalysis in Continuous Flow by Solid-Supported Peptidic Catalysts

(2012) Sándor B. Ötvös et al.   ChemSusChem

Therapeutic peptides

(2012) Fernando Albericio et al.   Future Medicinal Chemistry

Benzylic Phosphates as Electrophiles in the Palladium-Catalyzed Asymmetric Benzylation of Azlactones

(2012) Barry M. Trost et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Efficient Alkyl Ether Synthesis via Palladium-Catalyzed, Picolinamide-Directed Alkoxylation of Unactivated C(sp3)–H and C(sp2)–H Bonds at Remote Positions

(2012) Shu-Yu Zhang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Improved Protocol for Indoline Synthesis via Palladium-Catalyzed Intramolecular C(sp2)–H Amination

(2012) Gang He et al.   ORGANIC LETTERS

Palladium-catalyzed N-(2-pyridyl)sulfonyl-directed C(sp3)–H γ-arylation of amino acid derivatives

(2012) Nuria Rodríguez et al.   Chemical Science

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

(2011) Keary M. Engle et al.   ACCOUNTS OF CHEMICAL RESEARCH

A Practical Strategy for the Structural Diversification of Aliphatic Scaffolds through the Palladium-Catalyzed Picolinamide-Directed Remote Functionalization of Unactivated C(sp3)H Bonds

(2011) Gang He et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity

(2011) Yizhe Yan et al.   CHEMICAL COMMUNICATIONS

Asymmetric Strecker Reactions

(2011) Jun Wang et al.   CHEMICAL REVIEWS

Heterocycle Synthesis via Direct C–H/N–H Coupling

(2011) Enrico T. Nadres et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Highly Efficient Syntheses of Azetidines, Pyrrolidines, and Indolines via Palladium Catalyzed Intramolecular Amination of C(sp3)–H and C(sp2)–H Bonds at γ and δ Positions

(2011) Gang He et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Palladium-Catalyzed β Arylation of Carboxylic Esters

(2010) Alice Renaudat et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

C—H Bond Activation in Transition Metal Species from a Computational Perspective

(2010) David Balcells et al.   CHEMICAL REVIEWS

Functionalization of Organic Molecules by Transition-Metal-Catalyzed C(sp3)H Activation

(2010) Rodolphe Jazzar et al.   CHEMISTRY-A EUROPEAN JOURNAL

Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3−Csp) of Natural α-Amino Acids and Alkynes

(2010) Hai-Peng Bi et al.   JOURNAL OF ORGANIC CHEMISTRY

Nontraditional Reactions of Azomethine Ylides: Decarboxylative Three-Component Couplings of α-Amino Acids

(2010) Chen Zhang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Pd(II)-Catalyzedo-C−H Acetoxylation of Phenylalanine and Ephedrine Derivatives with MeCOOOtBu/Ac2O

(2010) Chris J. Vickers et al.   ORGANIC LETTERS

Functionalization of Aromatic Amino Acids via Direct C−H Activation: Generation of Versatile Building Blocks for Accessing Novel Peptide Space

(2010) Falco-Magnus Meyer et al.   ORGANIC LETTERS

The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids

(2009) Hai-Peng Bi et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Total Synthesis of Celogentin C by Stereoselective CH Activation

(2009) Yiqing Feng et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

(2009) Fabio Bellina et al.   CHEMICAL REVIEWS

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

(2009) Javier Ruiz-Rodríguez et al.   CHEMISTRY-A EUROPEAN JOURNAL

Peptidomimetics - A Versatile Route to Biologically Active Compounds

(2009) Andreas Grauer et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of CytochromecOxidase

(2009) Maximillian E. Mahoney et al.   JOURNAL OF ORGANIC CHEMISTRY

Pd(0)/PR3-Catalyzed Intermolecular Arylation of sp3C−H Bonds

(2009) Masayuki Wasa et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The catalytic ortho-arylation of tyrosine

(2009) Robin B. Bedford et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

A Novel Iron-Catalyzed Decarboxylative Csp3−Csp2Coupling of Proline Derivatives and Naphthol

(2009) Hai-Peng Bi et al.   ORGANIC LETTERS

Pd(II)-Catalyzed Cross-Coupling of sp3C−H Bonds with sp2and sp3Boronic Acids Using Air as the Oxidant

(2008) Dong-Hui Wang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY