Hydroaminoalkylation for the Catalytic Addition of Amines to Alkenes or Alkynes: Diverse Mechanisms Enable Diverse Substrate Scope

Intermolecular Hydroaminoalkylation of Alkynes

(2021) Tobias Kaper et al.   CHEMISTRY-A EUROPEAN JOURNAL

DFT Study on Zr-Catalyzed Alkene Hydroaminoalkylation: Origin of Regioselectivity, Diastereoselectivity, and Influence of Substrate

(2021) Ran Fang et al.   ORGANIC LETTERS

Ureate Titanium Catalysts for Hydroaminoalkylation: Using Ligand Design to Increase Reactivity and Utility

(2021) Manfred Manßen et al.   ACS Catalysis

Direct, Catalytic α-Alkylation of N-Heterocycles by Hydroaminoalkylation: Substrate Effects for Regiodivergent Product Formation

(2021) Rebecca C. DiPucchio et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines

(2021) Hannah E. Askey et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Photocatalytic Regioselective Direct Hydroaminoalkylation of Aryl-Substituted Alkenes with Amines

(2021) Natalia A. Larionova et al.   ORGANIC LETTERS

Ni-catalyzed hydroaminoalkylation of alkynes with amines

(2021) Wei-Wei Yao et al.   Nature Communications

Commodity Polymers to Functional Aminated Materials: Single-Step and Atom-Economic Synthesis by Hydroaminoalkylation

(2021) Sabrina S. Scott et al.   ACS Macro Letters

New Strategies for the Transition-Metal Catalyzed Synthesis of Aliphatic Amines

(2020) Aaron Trowbridge et al.   CHEMICAL REVIEWS

Iridium(I)-catalyzed α-C(sp3)–H Alkylation of Saturated Azacycles

(2020) Pritha Verma et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Site-Selective C–H Alkylation of Piperazine Substrates via Organic Photoredox Catalysis

(2020) Joshua B. McManus et al.   ORGANIC LETTERS

Dynamic Cross-Linking of Catalytically Synthesized Poly(Aminonorbornenes)

(2020) Nirmalendu Kuanr et al.   MACROMOLECULES

Metal-Ligand Cooperativity in Titanium Catalyzed Anti-Markovnikov Hydroamination

(2020) Han Hao et al.   ACS Catalysis

A Cyclic Ureate Tantalum Catalyst for Preferential Hydroaminoalkylation with Aliphatic Amines. Mechanistic Insights into Substrate Controlled Reactivity

(2020) Pargol Daneshmand et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A General Organocatalytic System for Enantioselective Radical Conjugate Additions to Enals

(2020) Emilien Le Saux et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Zirconium-Catalyzed Hydroaminoalkylation of Alkynes for the Synthesis of Allylic Amines

(2020) Erick Nuñez Bahena et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Regiodivergent Hydroaminoalkylation of Alkynes and Allenes via a Combined Rhodium and Photoredox Catalytic System

(2019) Bernhard Breit et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Photoredox-Catalyzed Site-Selective α-C(sp3 )−H Alkylation of Primary Amine Derivatives

(2019) Melissa A. Ashley et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Exploiting Natural Complexity: Synthetic Terpenoid‐Alkaloids by Regioselective and Diastereoselective Hydroaminoalkylation Catalysis

(2019) Rebecca C. DiPucchio et al.   ChemCatChem

Planar‐chiral [2.2]Paracyclophane‐based Pyridonates as Ligands for Tantalum‐catalyzed Hydroaminoalkylation

(2019) Carolin Braun et al.   ChemCatChem

α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines

(2019) Anirudra Paul et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design

(2019) Nathan J. Adamson et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Computational Investigation of Scandium-Based Catalysts for Olefin Hydroaminoalkylation and C–H Addition

(2019) Gen Luo et al.   ORGANOMETALLICS

Hydroaminoalkylation of Allenes

(2019) Jens Bielefeld et al.   SYNLETT

Hydroaminoalkylation/Buchwald-Hartwig amination sequences for the synthesis of benzo-annulated seven-membered nitrogen heterocycles

(2019) Tobias Kaper et al.   TETRAHEDRON

New Titanium Complexes and Their Use in Hydroamination and Hydroaminoalkylation Reactions

(2019) Jens Bielefeld et al.   EUROPEAN JOURNAL OF INORGANIC CHEMISTRY

Zirconium Hydroaminoalkylation. An Alternative Disconnection for the Catalytic Synthesis of α-Arylated Primary Amines

(2019) Ana Koperniku et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Titanium‐Catalyzed Hydroaminoalkylation of Ethylene

(2019) Michael Rosien et al.   CHEMISTRY-A EUROPEAN JOURNAL

Synthesis of beta-Substituted gamma-Aminobutyric Acid Derivatives via Enantioselective Photoredox Catalysis

(2018) Jiajia Ma et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Catalytic and Atom-Economic Csp3 −Csp3 Bond Formation: Alkyl Tantalum Ureates for Hydroaminoalkylation

(2018) Rebecca C. DiPucchio et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Tandem Hydroaminomethylation Reaction to Synthesize Amines from Alkenes

(2018) Philippe Kalck et al.   CHEMICAL REVIEWS

Remote C−H Activation of Various N-Heterocycles Using a Single Template

(2018) Guoqiang Yang et al.   CHEMISTRY-A EUROPEAN JOURNAL

Generation and Alkylation of α-Carbamyl Radicals via Organic Photoredox Catalysis

(2018) Joshua B. McManus et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer

(2018) Qilei Zhu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Scandium-catalyzed C(sp3)–H alkylation of N,N-dimethyl anilines with alkenes

(2018) Hongjie Gao et al.   Organic Chemistry Frontiers

Enantioselective remote meta-C–H arylation and alkylation via a chiral transient mediator

(2018) Hang Shi et al.   NATURE

Multicomponent synthesis of tertiary alkylamines by photocatalytic olefin-hydroaminoalkylation

(2018) Aaron Trowbridge et al.   NATURE

Titanium Catalysts with Linked Indenyl–Amido Ligands for Hydroamination and Hydroaminoalkylation Reactions

(2018) Stefan H. Rohjans et al.   ORGANOMETALLICS

Overcoming the Limitations of γ- and δ-C–H Arylation of Amines through Ligand Development

(2018) Yan-Qiao Chen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Ta-Catalyzed Hydroaminoalkylation of Alkenes: Insights into Ligand-Modified Reactivity Using DFT

(2018) Damon J. Gilmour et al.   ORGANOMETALLICS

A Mild Hydroaminoalkylation of Conjugated Dienes Using a Unified Cobalt and Photoredox Catalytic System

(2017) Scott M. Thullen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd–PHOX Catalyst

(2017) Nathan J. Adamson et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis

(2017) Faben A. Cruz et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

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

(2017) Peng Wang et al.   NATURE

Selective sp3 C–H alkylation via polarity-match-based cross-coupling

(2017) Chip Le et al.   NATURE

Direct α-C–H bond functionalization of unprotected cyclic amines

(2017) Weijie Chen et al.   Nature Chemistry

In Situ Generation of a Regio- and Diastereoselective Hydroaminoalkylation Catalyst Using Commercially Available Starting Materials

(2017) Peter M. Edwards et al.   ORGANIC LETTERS

Mechanistic Insights into Scandium-Catalyzed Hydroaminoalkylation of Olefins with Amines: Origin of Regioselectivity and Charge-Based Prediction Model

(2017) Fan Liu et al.   ORGANOMETALLICS

Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines

(2017) Andrew J. Musacchio et al.   SCIENCE

Thieme Chemistry Journals Awardees – Where Are They Now? Titanium-Catalyzed Hydroaminoalkylation of Vinylsilanes and a One-Pot Procedure for the Synthesis of 1,4-Benzoazasilines

(2017) Sven Doye et al.   SYNLETT

Amidate Complexes of Tantalum and Niobium for the Hydroaminoalkylation of Unactivated Alkenes

(2017) Jean Michel Lauzon et al.   ACS Catalysis

Ligand Effects and Kinetic Investigations of Sterically Accessible 2-Pyridonate Tantalum Complexes for Hydroaminoalkylation

(2017) Jason W. Brandt et al.   ACS Catalysis

Catalysis by Design: Well-Defined Single-Site Heterogeneous Catalysts

(2016) Jérémie D. A. Pelletier et al.   ACCOUNTS OF CHEMICAL RESEARCH

The medicinal chemist's toolbox for late stage functionalization of drug-like molecules

(2016) Tim Cernak et al.   CHEMICAL SOCIETY REVIEWS

One-Pot Procedure for the Synthesis of 1,5-Benzodiazepines fromN-Allyl-2-bromoanilines

(2016) Marco Weers et al.   CHEMISTRY-A EUROPEAN JOURNAL

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

Enantioselective amine α-functionalization via palladium-catalysed C–H arylation of thioamides

(2016) Pankaj Jain et al.   Nature Chemistry

First-Row Late Transition Metals for Catalytic (Formal) Hydro­amination of Unactivated Alkenes

(2016) Jérôme Hannedouche et al.   SYNTHESIS-STUTTGART

Scandium-catalysed intermolecular hydroaminoalkylation of olefins with aliphatic tertiary amines

(2016) Adi E. Nako et al.   Chemical Science

Diene hydroaminomethylation via ruthenium-catalyzed C–C bond forming transfer hydrogenation: beyond carbonylation

(2016) Susumu Oda et al.   Chemical Science

N,O-Chelating Four-Membered Metallacyclic Titanium(IV) Complexes for Atom-Economic Catalytic Reactions

(2015) Scott A. Ryken et al.   ACCOUNTS OF CHEMICAL RESEARCH

Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis

(2015) Joel W. Beatty et al.   ACCOUNTS OF CHEMICAL RESEARCH

An Aminopyridinato Titanium Catalyst for the Intramolecular Hydroaminoalkylation of Secondary Aminoalkenes

(2015) Jaika Dörfler et al.   ADVANCED SYNTHESIS & CATALYSIS

Isolation and Characterization of Well-Defined Silica-Supported Azametallacyclopentane: A Key Intermediate in Catalytic Hydroaminoalkylation Reactions

(2015) Bilel Hamzaoui et al.   ADVANCED SYNTHESIS & CATALYSIS

Hydroaminomethylation Beyond Carbonylation: Allene-Imine Reductive Coupling by Ruthenium-Catalyzed Transfer Hydrogenation

(2015) Susumu Oda et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Efficient Access to Titanaaziridines by CH Activation ofN-Methylanilines at Ambient Temperature

(2015) Manfred Manßen et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ligand-Enabled Catalytic CH Arylation of Aliphatic Amines by a Four-Membered-Ring Cyclopalladation Pathway

(2015) Chuan He et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Late Transition Metal-Catalyzed Hydroamination and Hydroamidation

(2015) Liangbin Huang et al.   CHEMICAL REVIEWS

Well-Defined Single-Site Monohydride Silica-Supported Zirconium from Azazirconacyclopropane

(2015) Bilel Hamzaoui et al.   CHEMISTRY-A EUROPEAN JOURNAL

Intermolecular hydroaminoalkylation of alkenes and dienes using a titanium mono(formamidinate) catalyst

(2015) Jaika Dörfler et al.   DALTON TRANSACTIONS

The direct arylation of allylic sp3 C–H bonds via organic and photoredox catalysis

(2015) James D. Cuthbertson et al.   NATURE

Catalytic asymmetric hydroamination of unactivated internal olefins to aliphatic amines

(2015) Y. Yang et al.   SCIENCE

Directed Ruthenium-Catalyzed C(sp3)H α-Alkylation of Cyclic Amines Using Dioxolane-Protected Alkenones

(2014) Artem A. Kulago et al.   ADVANCED SYNTHESIS & CATALYSIS

A 2,6-Bis(phenylamino)pyridinato Titanium Catalyst for the Highly Regioselective Hydroaminoalkylation of Styrenes and 1,3-Butadienes

(2014) Jaika Dörfler et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

anti-Markovnikov Hydroamination of Alkenes Catalyzed by a Two-Component Organic Photoredox System: Direct Access to Phenethylamine Derivatives

(2014) Tien M. Nguyen et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

A Commercially Available Tantalum Catalyst for the Highly Regioselective Intermolecular Hydroaminoalkylation of Styrenes

(2014) Jaika Dörfler et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

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

(2014) Edon Vitaku et al.   JOURNAL OF MEDICINAL CHEMISTRY

The Coupling of Tertiary Amines with Acrylate Derivatives via Visible-Light Photoredox Catalysis

(2014) Xiaojun Dai et al.   JOURNAL OF ORGANIC CHEMISTRY

2-Pyridonate Tantalum Complexes for the Intermolecular Hydroaminoalkylation of Sterically Demanding Alkenes

(2014) Eugene Chong et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin

(2014) Lingling Chu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Conformation-induced remote meta-C–H activation of amines

(2014) Ri-Yuan Tang et al.   NATURE

Ruthenium(II)-Catalyzed C(sp3)–H α-Alkylation of Pyrrolidines

(2014) Marvin Schinkel et al.   ORGANIC LETTERS

Unique Regioselectivity in the C(sp3)–H α-Alkylation of Amines: The Benzoxazole Moiety as a Removable Directing Group

(2014) Günther Lahm et al.   ORGANIC LETTERS

Hydroaminoalkylation: Early-Transition-Metal-Catalyzed α-Alkylation of Amines

(2014) Laurel Schafer et al.   SYNTHESIS-STUTTGART

Phosphoramidate Tantalum Complexes for Room-Temperature CH Functionalization: Hydroaminoalkylation Catalysis

(2013) Pierre Garcia et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ruthenium catalyzed hydroaminoalkylation of isoprene via transfer hydrogenation: byproduct-free prenylation of hydantoins

(2013) Daniel C. Schmitt et al.   CHEMICAL COMMUNICATIONS

Oxidative C–H amination reactions

(2013) Marie-Laure Louillat et al.   CHEMICAL SOCIETY REVIEWS

Titanium-Catalyzed Intermolecular Hydroaminoalkylation of Conjugated Dienes

(2013) Till Preuß et al.   CHEMISTRY-A EUROPEAN JOURNAL

TaMe3Cl2-Catalyzed Intermolecular Hydroaminoalkylation: A Simple Complex for Enhanced Reactivity and Expanded Substrate Scope

(2013) Zhengxing Zhang et al.   CHEMISTRY-A EUROPEAN JOURNAL

Removal of the Pyridine Directing Group from α-Substituted N-(Pyridin-2-yl)piperidines Obtained via Directed Ru-Catalyzed sp3 C–H Functionalization

(2013) Veerle Smout et al.   JOURNAL OF ORGANIC CHEMISTRY

Anti-Markovnikov Hydroamination of Alkenes Catalyzed by an Organic Photoredox System

(2013) Tien M. Nguyen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Tantalum Catalyzed Hydroaminoalkylation for the Synthesis of α- and β-Substituted N-Heterocycles

(2013) Philippa R. Payne et al.   ORGANIC LETTERS

2-Pyridonate Titanium Complexes for Chemoselectivity. Accessing Intramolecular Hydroaminoalkylation over Hydroamination

(2013) Eugene Chong et al.   ORGANIC LETTERS

Redox-Neutral α-Arylation of Amines

(2013) Weijie Chen et al.   ORGANIC LETTERS

Synthesis and Structure of Group 4 Symmetric Amidinate Complexes and Their Reactivity in the Polymerization of α-Olefins

(2013) Tatyana Elkin et al.   ORGANOMETALLICS

Aminopyridinato Titanium Catalysts for the Hydroaminoalkylation of Alkenes and Styrenes

(2012) Jaika Dörfler et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization

(2012) Percia Beatrice Arockiam et al.   CHEMICAL REVIEWS

The Role of the Alcohol and Carboxylic Acid in Directed Ruthenium-Catalyzed C(sp3)H α-Alkylation of Cyclic Amines

(2012) Sheba D. Bergman et al.   CHEMISTRY-A EUROPEAN JOURNAL

Direct α-Functionalization of Saturated Cyclic Amines

(2012) Emily A. Mitchell et al.   CHEMISTRY-A EUROPEAN JOURNAL

Tantallaaziridines: from synthesis to catalytic applications

(2012) Jean Michel P. Lauzon et al.   DALTON TRANSACTIONS

The Mechanism of Hydroaminoalkylation Catalyzed by Group 5 Metal Binaphtholate Complexes

(2012) Alexander L. Reznichenko et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Visible-Light-Mediated Utilization of α-Aminoalkyl Radicals: Addition to Electron-Deficient Alkenes Using Photoredox Catalysts

(2012) Yoshihiro Miyake et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Dinuclear Titanium Complexes with Sulfamide Ligands as Precatalysts for Hydroaminoalkylation and Hydroamination Reactions

(2012) Sven Doye et al.   SYNLETT

Cationic iridium-catalyzed enantioselective activation of secondary sp3 C–H bond adjacent to nitrogen atom

(2012) Shiguang Pan et al.   TETRAHEDRON

The Mechanism of the Titanium-Catalyzed Hydroaminoalkylation of Alkenes

(2011) Insa Prochnow et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Recent Advances in Amine Synthesis by Catalytic Hydroaminomethylation of Alkenes

(2011) Delphine Crozet et al.   ChemCatChem

Transition metal-catalyzed arylation of unactivated C(sp3)–H bonds

(2011) Olivier Baudoin   CHEMICAL SOCIETY REVIEWS

Synthesis and catalytic activity of group 5 metal amides with chiral biaryldiamine-based ligands

(2011) Furen Zhang et al.   DALTON TRANSACTIONS

Mechanistic Elucidation of Intramolecular Aminoalkene Hydroamination Catalyzed by a Tethered Bis(ureate) Complex: Evidence for Proton-Assisted C–N Bond Formation at Zirconium

(2011) David C. Leitch et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Group 5 Metal Binaphtholate Complexes for Catalytic Asymmetric Hydroaminoalkylation and Hydroamination/Cyclization

(2011) Alexander L. Reznichenko et al.   ORGANOMETALLICS

Discovery of an  -Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity

(2011) A. McNally et al.   SCIENCE

[Ind2TiMe2]: A Catalyst for the Hydroaminomethylation of Alkenes and Styrenes

(2010) Raphael Kubiak et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Highly enantioselective hydroaminoalkylation of secondary amines catalyzed by group 5 metal amides with chiral biarylamidate ligands

(2010) Guofu Zi et al.   CHEMICAL COMMUNICATIONS

C-2 Arylation of Piperidines through Directed Transition-Metal-Catalyzed sp3CH Activation

(2010) Hana Prokopcová et al.   CHEMISTRY-A EUROPEAN JOURNAL

Tantalum-Amidate Complexes for the Hydroaminoalkylation of Secondary Amines: Enhanced Substrate Scope and Enantioselective Chiral Amine Synthesis

(2009) Patrick Eisenberger et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Titanium-Catalyzed Hydroaminoalkylation of Alkenes by CH Bond Activation at sp3Centers in the α-Position to a Nitrogen Atom

(2009) Raphael Kubiak et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Catalytic Hydroaminoalkylation

(2009) Peter W. Roesky   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Tetrabenzyltitanium: An Improved Catalyst for the Activation of sp3CH Bonds Adjacent to Nitrogen Atoms

(2009) Insa Prochnow et al.   ChemCatChem

Selective C−H Activation α to Primary Amines. Bridging Metallaaziridines for Catalytic, Intramolecular α-Alkylation

(2009) Jason A. Bexrud et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Hydroamination: Direct Addition of Amines to Alkenes and Alkynes

(2008) Thomas E. Müller et al.   CHEMICAL REVIEWS

Hydroaminoalkylation of Unactivated Olefins with Dialkylamines

(2008) Seth B. Herzon et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY