Palladium-Catalyzed Nondirected Late-Stage C–H Deuteration of Arenes

Catalytic Hydrogen Isotope Exchange Reactions in Late-Stage Functionalization

(2021) Qi-Kai Kang et al.   SYNLETT

Site-Selective Silver-Catalyzed C–H Bond Deuteration of Five-Membered Aromatic Heterocycles and Pharmaceuticals

(2021) Adrian Tlahuext-Aca et al.   ACS Catalysis

Mechanism of the Arene‐Limited Nondirected C–H Activation of Arenes with Palladium

(2021) Philipp Wedi et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Late-Stage β-C(sp3)–H Deuteration of Carboxylic Acids

(2021) Alexander Uttry et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

C−H Functionalization-Prediction of Selectivity in Iridium(I)-Catalyzed Hydrogen Isotope Exchange Competition Reactions

(2020) Mégane Valero et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Base metal-catalyzed hydrogen isotope exchange

(2020) Haifeng Yang et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

meta‐Selective C–H Arylation of Fluoroarenes and Simple Arenes

(2020) Luo-Yan Liu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Sterically Controlled C−H Olefination of Heteroarenes

(2020) Hao Chen et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Deuterium Exchange between Arenes and Deuterated Solvents in the Absence of a Transition Metal: Synthesis of D-Labeled Fluoroarenes

(2020) Vanesa Salamanca et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Multiple Site Hydrogen Isotope Labelling of Pharmaceuticals

(2020) Marion Daniel-Bertrand et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Hydrogen Isotope Exchange with Superbulky Alkaline Earth Metal Amide Catalysts

(2020) Johannes Martin et al.   ACS Catalysis

C(sp2)–H Activation with Pyridine Dicarbene Iron Dialkyl Complexes: Hydrogen Isotope Exchange of Arenes Using Benzene-d6 as a Deuterium Source

(2020) Javier Corpas et al.   ACS Catalysis

Catalyst Controlled Regiodivergent C‐H Alkynylation of Thiophenes

(2020) Arup Mondal et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Shifted Selectivity in Protonation Enables the Mild Deuteration of Arenes Through Catalytic Amounts of Bronsted Acids in Deuterated Methanol

(2020) Oliver Fischer et al.   JOURNAL OF ORGANIC CHEMISTRY

Facile H/D Exchange at (Hetero)Aromatic Hydrocarbons Catalyzed by a Stable Trans-Dihydride N-Heterocyclic Carbene (NHC) Iron Complex

(2020) Subhash Garhwal et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Efficient Continuous-Flow H–D Exchange Reaction of Aromatic Nuclei in D2O/2-PrOH Mixed Solvent in Catalyst Cartridge Packed with Platinum on Carbon Beads

(2020) Kwihwan Park et al.   BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN

Applications of deuterium in medicinal chemistry

(2019) Tracey Pirali et al.   JOURNAL OF MEDICINAL CHEMISTRY

Dual Ligand-Enabled Nondirected C–H Cyanation of Arenes

(2019) Hao Chen et al.   ACS Catalysis

H–D Exchange Deuteration of Arenes at Room Temperature

(2019) Yoshinari Sawama et al.   ORGANIC PROCESS RESEARCH & DEVELOPMENT

para-Selective C-H Olefination of Aniline Derivatives via Pd/S,O-Ligand Catalysis

(2019) Kananat Naksomboon et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Ni(I)–X Complexes Bearing a Bulky α-Diimine Ligand: Synthesis, Structure, and Superior Catalytic Performance in the Hydrogen Isotope Exchange in Pharmaceuticals

(2019) Cayetana Zarate et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Palladium‐Catalyzed Selective meta ‐C−H Deuteration of Arenes: Reaction Design and Applications

(2019) Sukdev Bag et al.   CHEMISTRY-A EUROPEAN JOURNAL

Directed Iridium‐Catalyzed Hydrogen Isotope Exchange Reactions of Phenylacetic Acid Esters and Amides

(2019) Mégane Valero et al.   CHEMISTRY-A EUROPEAN JOURNAL

Palladium-Catalyzed Remote meta-C–H Bond Deuteration of Arenes Using a Pyridine Template

(2019) Hui Xu et al.   ORGANIC LETTERS

Ag2CO3-Catalyzed H/D Exchange of Five-Membered Heteroarenes at Ambient Temperature

(2019) En-Ci Li et al.   ORGANIC LETTERS

Recent Advances in Iridium(I) Catalysis towards Directed Hydrogen Isotope Exchange

(2019) William J. Kerr et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

Sterically Controlled Late-Stage C–H Alkynylation of Arenes

(2019) Arup Mondal et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Metal–Metal Synergy in Well-Defined Surface Tantalum–Iridium Heterobimetallic Catalysts for H/D Exchange Reactions

(2019) Sébastien Lassalle et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

NHC-Stabilized Iridium Nanoparticles as Catalysts in Hydrogen Isotope Exchange Reactions of Anilines

(2019) Mégane Valero et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ruthenium(II)‐Catalyzed Hydrogen Isotope Exchange of Pharmaceutical Drugs by C−H Deuteration and C−H Tritiation

(2019) Valentin Müller et al.   ChemCatChem

The Arene-Limited Nondirected C-H Activation of Arenes

(2018) Philipp Wedi et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Dual Ligand-Enabled Nondirected C−H Olefination of Arenes

(2018) Hao Chen et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Deuterium- and Tritium-Labelled Compounds: Applications in the Life Sciences

(2018) Jens Atzrodt et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

C−H Functionalisation for Hydrogen Isotope Exchange

(2018) Jens Atzrodt et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

(2018) Carlo Sambiagio et al.   CHEMICAL SOCIETY REVIEWS

Site-Selective Nickel-Catalyzed Hydrogen Isotope Exchange in N-Heterocycles and Its Application to the Tritiation of Pharmaceuticals

(2018) Haifeng Yang et al.   ACS Catalysis

Ligand-Promoted Non-Directed C−H Cyanation of Arenes

(2018) Luo-Yan Liu et al.   CHEMISTRY-A EUROPEAN JOURNAL

Palladium-Catalyzed Late-Stage Direct Arene Cyanation

(2018) Da Zhao et al.   Chem

Hydrogen-Isotope Exchange (HIE) Reactions of Secondary and Tertiary Sulfonamides and Sulfonylureas with Iridium(I) Catalysts

(2017) Annina Burhop et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Ligand-accelerated non-directed C–H functionalization of arenes

(2017) Peng Wang et al.   NATURE

FDA approves first deuterated drug

(2017) Asher Mullard   NATURE REVIEWS DRUG DISCOVERY

S,O-Ligand-Promoted Palladium-Catalyzed C–H Functionalization Reactions of Nondirected Arenes

(2017) Kananat Naksomboon et al.   ACS Catalysis

Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions: C–H activation of unprotected tetrazoles

(2016) William J. Kerr et al.   CHEMICAL COMMUNICATIONS

Mono and dimetallic pyrene-imidazolylidene complexes of iridium(iii) for the deuteration of organic substrates and the C–C coupling of alcohols

(2016) S. Ibañez et al.   DALTON TRANSACTIONS

Synthesis and selective2H-,13C-, and15N-labeling of the Tau protein binder THK-523

(2016) Karoline T. Neumann et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

Vibrational Mode Assignment of α-Pinene by Isotope Editing: One Down, Seventy-One To Go

(2016) Mary Alice Upshur et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Iron-catalysed tritiation of pharmaceuticals

(2016) Renyuan Pony Yu et al.   NATURE

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

(2016) John F. Hartwig et al.   ACS Central Science

Isotope chemistry; a useful tool in the drug discovery arsenal

(2015) Charles S. Elmore et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Selective catalytic deuteration of phosphorus ligands using ruthenium nanoparticles: a new approach to gain information on ligand coordination

(2015) Emma Bresó-Femenia et al.   CHEMICAL COMMUNICATIONS

Mechanistic considerations on catalytic H/D exchange mediated by organometallic transition metal complexes

(2015) Andrea Di Giuseppe et al.   COMPTES RENDUS CHIMIE

A Simple and Cost-Effective Method for the Regioselective Deuteration of Phenols

(2015) Miao Zhan et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Harnessing C–H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization

(2015) Venkata A Kallepalli et al.   JOURNAL OF ORGANIC CHEMISTRY

H–D exchange in deuterated trifluoroacetic acid via ligand-directed NHC–palladium catalysis: a powerful method for deuteration of aromatic ketones, amides, and amino acids

(2015) Richard Giles et al.   TETRAHEDRON LETTERS

The Synthesis of Highly Active Iridium(I) Complexes and their Application in Catalytic Hydrogen Isotope Exchange

(2014) Jack A. Brown et al.   ADVANCED SYNTHESIS & CATALYSIS

Hydrogen/deuterium exchange of cross-linkable α-amino acid derivatives in deuterated triflic acid

(2014) Lei Wang et al.   BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY

Synthesis of deuterium-labelled fluorobenzoic acids to be used as internal standards in isotope dilution mass spectrometry

(2014) Karsten Müller et al.   ISOTOPES IN ENVIRONMENTAL AND HEALTH STUDIES

Proton or Metal? The H/D Exchange of Arenes in Acidic Solvents

(2014) Dominik Munz et al.   ACS Catalysis

Palladium-Catalyzedortho-Selective CH Deuteration of Arenes: Evidence for Superior Reactivity of Weakly Coordinated Palladacycles

(2013) Sandy Ma et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Regioselective and Stereospecific Deuteration of Bioactive Aza Compounds by the Use of Ruthenium Nanoparticles

(2013) Grégory Pieters et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Rapid and Controllable Hydrogen/Deuterium Exchange on Aromatic Rings of α-Amino Acids and Peptides

(2013) Yuta Murai et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Using Deuterium in Drug Discovery: Leaving the Label in the Drug

(2013) Thomas G. Gant   JOURNAL OF MEDICINAL CHEMISTRY

Development of Deuterium Labeling Method Based on the Heterogeneous Platinum Group Metal-Catalyzed C-H Activation

(2013) Hironao Sajiki   YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN

On the Interpretation of Deuterium Kinetic Isotope Effects in CH Bond Functionalizations by Transition-Metal Complexes

(2012) Eric M. Simmons et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Beyond Directing Groups: Transition-Metal-Catalyzed CH Activation of Simple Arenes

(2012) Nadine Kuhl et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Use of Radiolabeled Compounds in Drug Metabolism and Pharmacokinetic Studies

(2012) Emre M. Isin et al.   CHEMICAL RESEARCH IN TOXICOLOGY

A two-step synthesis of deuterium labeled 8, 8, 9, 9-d4-hexadecane from nonanoic acid

(2012) Lei Zhou et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

Catalytic Arene H/D Exchange with Novel Rhodium and Iridium Complexes

(2012) Jennifer L. Rhinehart et al.   ORGANOMETALLICS

H/D Exchange Processes Catalyzed by an Iridium-Pincer Complex

(2011) Vlad M. Iluc et al.   ORGANOMETALLICS

Regioselective deuteration of 25,27-dialkoxycalix[4]arenes

(2011) Michaela Mačková et al.   TETRAHEDRON LETTERS

Platinum and Palladium Complexes Containing Cationic Ligands as Catalysts for Arene H/D Exchange and Oxidation

(2010) Marion H. Emmert et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Pd- and Pt-catalyzed H/D exchange methods and their application for internal MS standard preparation from a Sanofi-Aventis perspective

(2010) Jens Atzrodt et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

Metal-catalysed hydrogen isotope exchange labelling: a brief overview

(2010) William J. S. Lockley et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

The development and use of novel iridium complexes as catalysts for ortho-directed hydrogen isotope exchange reactions

(2010) Göran N. Nilsson et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

Metal-catalysed isotopic exchange labelling: 30 years of experience in pharmaceutical R&D

(2010) Paul H. Allen et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

Hydrogen-Deuterium Exchange Reactions of Aromatic Compounds and Heterocycles by NaBD4-Activated Rhodium, Platinum and Palladium Catalysts

(2009) Volker Derdau et al.   CHEMISTRY-A EUROPEAN JOURNAL

Quantitative Assay for the Direct Comparison of Platinum Catalysts in Benzene H/D Exchange

(2009) Amanda J. Hickman et al.   ORGANOMETALLICS

Application of Stable Isotope-Labeled Compounds in Metabolism and in Metabolism-Mediated Toxicity Studies

(2008) Abdul E. Mutlib   CHEMICAL RESEARCH IN TOXICOLOGY

Syntheses of (R,S)-naproxen and its 6-O-desmethylated metabolite labelled with2H

(2008) E. Fontana et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

A Simple, Cost-Effective Method for the Regioselective Deuteration of Anilines

(2008) Andrew Martins et al.   ORGANIC LETTERS

C−H Bond Activation by Rhodium(I) Phenoxide and Acetate Complexes: Mechanism of H−D Exchange between Arenes and Water

(2008) Susan Kloek Hanson et al.   ORGANOMETALLICS