4.8 Article

Coordination assembly enables highly selective catalytic hydroaminomethylation of olefins

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

A Selective and General Cobalt-Catalyzed Hydroaminomethylation of Olefins to Amines

Ji Yang et al.

Summary: A new cobalt catalyst has been developed for the domino hydroformylation-reductive amination reaction of olefins, showing excellent regioselectivity under mild conditions. The Co-tert-BuPy-Xantphos catalyst is more selective than traditional cobalt(I) catalysts and even outperforms most known rhodium catalysts.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Review Chemistry, Multidisciplinary

Operando monitoring of mechanisms and deactivation of molecular catalysts

Katrin Koehnke et al.

Summary: Observing and understanding the reaction mechanisms and catalyst deactivation in molecular catalysis is a challenging task in green chemistry. Operando experimental setups, which rely on spectroscopic analysis and chromatographic techniques, have the potential to elucidate these mechanisms. This review covers different spectroscopic techniques for monitoring molecular transition metal catalysts in solution and numerical methods to analyze the complex signals. Examples of industrially relevant chemical reactions demonstrate the importance of operando studies in developing stable and selective catalysts for greener processes.

GREEN CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Synthesis of rac-α-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst

Peng Gao et al.

Summary: This work presents the preparation and synthetic application of a class of water-soluble PNP ligands. These ligands were incorporated into catalysts and successfully used for the regioselective hydroformylation of arylalkenes, providing efficient access to α-aryl propionaldehydes with high yield and selectivity. The synthetic methodology was further demonstrated through gram-scale synthesis and diverse transformations for non-steroidal antiinflammatory drugs.

CHINESE CHEMICAL LETTERS (2022)

Article Multidisciplinary Sciences

Recyclable cooperative catalyst for accelerated hydroaminomethylation of hindered amines in a continuous segmented flow reactor

Malek Y. S. Ibrahim et al.

Summary: In this study, a rapid and reusable catalyst was developed for the selective production of hindered amines in a flow reactor. Online reaction optimization and solvent tuning enabled the switch between amine and enamine production without changing the ligand. Furthermore, a robust recovery strategy for the rhodium catalyst was demonstrated using its ionic nature.

NATURE COMMUNICATIONS (2022)

Article Chemistry, Physical

Efficient hydroaminomethylation of olefins catalyzed by Rh-complex ligated by P,O-hybrid ligand with chelating effect

Xiao-Chao Chen et al.

Summary: This study developed a new P,O-hybrid ligand and successfully synthesized a stable Rh-complex Z, which exhibited excellent catalytic activity to accelerate each individual step in the tandem hydroaminomethylation (HAM) reaction and inhibit the side-reaction of olefin-hydrogenation.

JOURNAL OF CATALYSIS (2022)

Article Chemistry, Multidisciplinary

A biphosphine copolymer encapsulated single-site Rh catalyst for heterogeneous regioselective hydroaminomethylation of alkenes

Kang Zhao et al.

Summary: A novel porous organic polymer catalyst was developed for the heterogeneous hydroaminomethylation of alkenes, resulting in improved regioselectivity.

CHEMICAL COMMUNICATIONS (2022)

Article Chemistry, Multidisciplinary

Water-soluble diphosphine ligands for rhodium-catalyzed branch-selective hydroaminomethylation of vinyl arenes with anilines in water

Luyun Zhang et al.

Summary: This study achieves the hydroaminomethylation of various vinyl arenes with anilines using water as the reaction media and rhodium catalyst. The water-soluble diphosphine ligands derived from bis(2-(diphenylphosphaneyl)ethyl)amides are used to facilitate the reaction. The methodology shows a wide scope of substrates and high selectivities, resulting in good yields of N-(2-phenylpropyl)anilines. Mechanistic studies reveal the imine hydrogenation reactivity of the catalysts through competition experiments and isotope labeling.

GREEN CHEMISTRY (2022)

Review Chemistry, Multidisciplinary

A Type of Structurally Adaptable Aromatic Spiroketal Based Chiral Diphosphine Ligands in Asymmetric Catalysis

Xiaoming Wang et al.

Summary: The research group developed an efficient synthesis of chiral aromatic spiroketals and corresponding diphosphine ligands, which exhibit unique adaptable structures and outstanding catalytic performance in transition metal complexes. The SKP ligands have shown remarkable versatility in coordinating with various transition metals and have demonstrated excellent efficiency in challenging asymmetric transformations, indicating their potential in advancing asymmetric catalysis.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

Article Chemistry, Multidisciplinary

Aqueous Biphasic Hydroaminomethylation Enabled by Methylated Cyclodextrins: Sensitivity Analysis for Transfer into a Continuous Process

Kai U. Kuennemann et al.

Summary: This study scaled up the highly regioselective Hydroaminomethylation (HAM) of 1-decene with diethylamine for a potential continuous process application. By adding cyclodextrins as a green mass transfer agent, the reaction rate and selectivity towards linear amines were successfully increased. Various parameters influencing the stability and activity of the system were investigated.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2021)

Editorial Material Chemistry, Multidisciplinary

Are Amines the Holy Grail for Facilitating CO2 Reduction?

Joakim B. Jakobsen et al.

Summary: The reduction of carbon dioxide is crucial for producing non-fossil-fuel-based feedstocks and mitigating greenhouse gas emissions. Amines play a critical role in these transformations, acting as CO2 trapping agents, proton shuttles, electron donors, and facilitators of CO2 reductions through formamide derivatives.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

Insight into decomposition of formic acid to syngas required for Rh-catalyzed hydroformylation of olefins

Lei Liu et al.

Summary: In this study, the behavior of formic acid (FA) in releasing H-2 and CO was carefully investigated, leading to the development of a new hydroformylation protocol without the need for syngas. The use of FA as a syngas source suppressed side reactions and enabled insight into the catalytic mechanism through spectroscopic analysis. This research provides a promising alternative for olefin hydroformylation with potential environmental benefits.

JOURNAL OF CATALYSIS (2021)

Article Chemistry, Physical

Selective Transformation of Vicinal Glycols to α-Hydroxy Acetates in Water via a Dehydrogenation and Oxidization Relay Process by a Self-Supported Single-Site Iridium Catalyst

Lingyun Shen et al.

Summary: A new solid self-supported NHC-Ir single-site catalyst was discovered in this study, which can efficiently convert alkyl and aryl vicinal glycols to alpha-hydroxy acetates in water. The catalyst shows much higher efficiency than other molecular catalysts, and density functional theory calculations reveal the mechanism of the reaction, demonstrating the potential of this protocol in the valorization of diols.

ACS CATALYSIS (2021)

Article Engineering, Environmental

Continuous co-product separation by organic solvent nanofiltration for the hydroaminomethylation in a thermomorphic multiphase system

Stefan Schluter et al.

Summary: This study developed a hybrid, continuous reaction and separation process for catalytic auto-tandem hydro-aminomethylation (HAM) reaction, demonstrating efficient production of valuable higher aliphatic amines and avoidance of product accumulation through effective separation and reuse of active catalyst. With an integrated catalyst recycling strategy and membrane-based separation of co-product, the process operated continuously for 75 hours, showing stable process operation and high catalyst rejection rates.

CHEMICAL ENGINEERING JOURNAL (2021)

Article Chemistry, Physical

Highly regioselective homogeneous isomerization-hydroformylation of 2-butene with water- and air-stable phosphoramidite bidentate ligand

Songbai Tang et al.

Summary: The highly selective isomerization-hydroformylation of 2-butene was achieved using a specific ligand and catalyst, resulting in a higher molar ratio of n- to isovaleraldehyde compared to reported systems. The structure and strong pi-acceptor ability of the ligand played a key role in enhancing reaction rate and selectivity, while the catalytic system proved to be stable during multiple recycling runs.

MOLECULAR CATALYSIS (2021)

Article Chemistry, Physical

Atomically dispersed Rh on hydroxyapatite as an effective catalyst for tandem hydroaminomethylation of olefins

Xiao Li et al.

Summary: The study demonstrates that the single-atom Rh catalyst supported on HAP shows high efficiency and good selectivity in the tandem hydroaminomethylation process. In this research, the 0.5Rh1/HAP catalyst not only achieved high conversion rates and selectivity, but also produced various corresponding amines from a wide range of substrates.

MOLECULAR CATALYSIS (2021)

Review Chemistry, Multidisciplinary

Metal-organic frameworks as catalytic selectivity regulators for organic transformations

Jun Guo et al.

Summary: Metal-organic frameworks (MOFs) have shown promising effects in regulating and improving selectivity in organic transformations, by manipulating their catalytic microenvironments. Researchers aim to utilize MOFs for the design and synthesis of high value-added organic chemicals.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Multidisciplinary

Heterogeneous Ru/TiO2 for hydroaminomethylation of olefins: multicomponent synthesis of amines

Jinghua An et al.

Summary: An efficient heterogeneous Ru/TiO2-catalyzed HAM reaction of olefins has been developed without any additives, leading to the successful synthesis of various amines and transformation of nitrobenzene derivatives in high yields.

GREEN CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Fast Titanium-Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine

Jens Bielefeld et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Multidisciplinary Sciences

Highly active cationic cobalt(II) hydroformylation catalysts

Drew M. Hood et al.

SCIENCE (2020)

Article Chemistry, Multidisciplinary

Selective Catalytic Dehydrogenative Oxidation of Bio-Polyols to Lactic Acid

Jiajie Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Glycerol Boosted Rh-Catalyzed Hydroaminomethylation Reaction: A Mechanistic Insight

Alejandro Serrano-Maldonado et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Review Multidisciplinary Sciences

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

Jose R. Cabrero-Antonino et al.

NATURE COMMUNICATIONS (2020)

Article Chemistry, Physical

Main element chemistry enables gas-cylinder-free hydroformylations

Samuel K. Pedersen et al.

NATURE CATALYSIS (2020)

Review Chemistry, Multidisciplinary

Catalytic reductive aminations using molecular hydrogen for synthesis of different kinds of amines

Kathiravan Murugesan et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Chemistry, Multidisciplinary

A Multicatalytic Approach to the Hydroaminomethylation of α-Olefins

Steven Hanna et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Reusable N-Heterocyclic Carbene Complex Catalysts and Beyond: A Perspective on Recycling Strategies

Wenlong Wang et al.

CHEMICAL REVIEWS (2018)

Review Chemistry, Multidisciplinary

Tandem Hydroaminomethylation Reaction to Synthesize Amines from Alkenes

Philippe Kalck et al.

CHEMICAL REVIEWS (2018)

Review Chemistry, Physical

Supramolecular Approaches To Control Activity and Selectivity in Hydroformylation Catalysis

Sandra S. Nurttila et al.

ACS CATALYSIS (2018)

Article Chemistry, Multidisciplinary

Rhodium-Complex-Catalyzed Hydroformylation of Olefins with CO2 and Hydrosilane

Xinyi Ren et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Production of Primary Amines by Reductive Amination of Biomass-Derived Aldehydes/Ketones

Guanfeng Liang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective

Rui Zhong et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

Fluorescent Pyrene-Based Bis-azole Compounds: Synthesis and Photophysical Analysis

Susana Ibanez et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

Review Chemistry, Multidisciplinary

Deactivation in Homogeneous Transition Metal Catalysis: Causes, Avoidance, and Cure

Robert H. Crabtree

CHEMICAL REVIEWS (2015)

Article Chemistry, Multidisciplinary

Phosphine- and Hydrogen-Free: Highly Regioselective Ruthenium-Catalyzed Hydroaminomethylation of Olefins

Samet Guelak et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Review Chemistry, Organic

rDeveiewsign and Development of Ligands for Palladium-Catalyzed Carbonylation Reactions

Weiwei Fang et al.

SYNTHESIS-STUTTGART (2014)

Article Multidisciplinary Sciences

Efficient selective and atom economic catalytic conversion of glycerol to lactic acid

Liam S. Sharninghausen et al.

NATURE COMMUNICATIONS (2014)

Article Chemistry, Multidisciplinary

Efficient and Regioselective Ruthenium-catalyzed Hydroaminomethylation of Olefins

Lipeng Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Review Multidisciplinary Sciences

Applications of Acceptorless Dehydrogenation and Related Transformations in Chemical Synthesis

Chidambaram Gunanathan et al.

SCIENCE (2013)

Review Chemistry, Multidisciplinary

N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union

George C. Fortman et al.

CHEMICAL SOCIETY REVIEWS (2011)

Review Chemistry, Multidisciplinary

Self-Supported Catalysts

Zheng Wang et al.

CHEMICAL REVIEWS (2009)

Article Chemistry, Multidisciplinary

Hydroaminomethylation with novel rhodium-carbene complexes: An efficient catalytic approach to pharmaceuticals

Moballigh Ahmed et al.

CHEMISTRY-A EUROPEAN JOURNAL (2007)

Article Chemistry, Multidisciplinary

Chiral metal-organic assemblies - A new approach to immogbilizing homogeneous asymmetric catalysts

LX Dai

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

Article Chemistry, Organic

Hydroaminomethylation of olefins using a rhodium carbene catalyst

AM Seayad et al.

TETRAHEDRON LETTERS (2003)

Article Multidisciplinary Sciences

Internal olefins to linear amines

A Seayad et al.

SCIENCE (2002)