Nucleophilic Aliphatic Substitution 2020 DOI
J. G. Moloney, Mark G. Moloney

Organic Reaction Mechanisms/Organic reaction mechanisms, Journal Year: 2024, Volume and Issue: unknown, P. 237 - 266

Published: March 15, 2024

Multilevel quantum mechanics and molecular calculations have been used to investigate the double inversion mechanism of nucleophilic substitution reaction F - + NH 2 Cl in aqueous solution. The nickel-catalyzed generation homoenolates by decarbonylation cyclic anhydrides their cross-coupling with unactivated alkyl bromides has access substituted aliphatic acids. acetoxy derivative (77b) galiellalactone (77a) smoothly undergoes a stereoretentive at tetrasubstituted carbon, using primary amine thiol nucleophiles or alcohols, presence catalytic amounts DMAP. reactions proceed initial allylic form new Michael acceptor, followed addition second equivalent nucleophile then retro-Michael restore unsaturated system.

Language: Английский

A Fe single atom on N,S-doped carbon catalyst for performing N-alkylation of aromatic amines under solvent-free conditions DOI
Guoping Lu,

Hongbin Shan,

Yamei Lin

et al.

Journal of Materials Chemistry A, Journal Year: 2021, Volume and Issue: 9(44), P. 25128 - 25135

Published: Jan. 1, 2021

A green and gram-scale strategy has been developed for the synthesis of Fe single atom/N,S-doped carbon catalyst via pyrolysis polyaniline-modified Fe,S-doped ZIFs, in which ZIFs can be prepared water at room temperature.

Language: Английский

Citations

61

Single Pd–Sx Sites In Situ Coordinated on CdS Surface as Efficient Hydrogen Autotransfer Shuttles for Highly Selective Visible-Light-Driven C–N Coupling DOI
Feng Niu, Wenguang Tu, Xinxin Lu

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(8), P. 4481 - 4490

Published: April 1, 2022

Selective synthesis of valuable secondary amines through N-alkylation with alcohols is an important reaction in the modern industry but still remains a challenge chemical technique. Hereby, we report visible-light-driven photocatalytic aniline benzyl alcohol over defined single Pd–Sx species situ coordinated on CdS surface. Encouragingly, conversion 100% and almost product selectivity toward amine N-benzylaniline are obtained impressive H2 production (11.8 mmol gcat–1 h–1). The mechanistic studies reveal that surface can trap photogenerated electrons to endow them long lifetime benefit vibrational coupling hydrogen adsorption then serve as efficient autotransfer shuttle for hydrogenation process formation N-benzylaniline. In addition, present catalyst possesses good substrate tolerance different substituted under optimized conditions. This work offers alternative solar-driven catalytic system mild

Language: Английский

Citations

52

Advances in One-Pot Chiral Amine Synthesis Enabled by Amine Transaminase Cascades: Pushing the Boundaries of Complexity DOI Creative Commons
Sam Mathew, Dominik Renn, Magnus Rueping

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(8), P. 5584 - 5598

Published: April 10, 2023

Amine transaminases constitute an important class of enzymes for the synthesis chiral amines, which are commonly used as building blocks in pharmaceutical compounds and fine chemicals. Over past decade, developments enzyme discovery process protein engineering have advanced use organic synthesis. Recent advances enzymatic cascade attracted attention due to efficient environmentally friendly routes synthesize amines. Enzymatic cascades can reduce traditional multistep enabled generation products from cheap starting materials. This review focuses on amine by chemoenzymatic utilizing transaminases.

Language: Английский

Citations

23

Synergistic roles of platinum nanoparticles and sodium ions within beta zeolites in N-alkylation of amines with aromatic alcohols DOI
Yue Wu, Shibo Xi, Cailing Chen

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(9), P. 2690 - 2699

Published: Aug. 9, 2023

Language: Английский

Citations

21

Zn(II)-Catalyzed Selective N-Alkylation of Amines with Alcohols Using Redox Noninnocent Azo-Aromatic Ligand as Electron and Hydrogen Reservoir DOI
Subhajit Chakraborty, Rakesh Mondal, Subhasree Pal

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(2), P. 771 - 787

Published: Dec. 28, 2022

We report a sustainable and eco-friendly approach for selective N-alkylation of various amines by alcohols, catalyzed well-defined Zn(II)-catalyst, Zn(La)Cl2 (1a), bearing tridentate arylazo scaffold. A total 57 N-alkylated were prepared in good to excellent yields, out which 17 examples are new. The Zn(II)-catalyst shows wide functional group tolerance, is compatible with the synthesis dialkylated via double diamines, produces precursors high yields marketed drugs tripelennamine thonzonium bromide gram-scale reactions. Control reactions DFT studies indicate that electron transfer events occur at azo-chromophore throughout catalytic process, shuttles between neutral azo, one-electron reduced azo-anion radical, two-electron hydrazo forms acting both as hydrogen reservoir, enabling reaction.

Language: Английский

Citations

26

Unraveling defect chemistry in doped-ceria catalyst for oxidative coupling of lignin-based aniline and benzyl alcohol DOI

Rong Shang,

Yulong Li,

Junjing Guo

et al.

Journal of Catalysis, Journal Year: 2024, Volume and Issue: 434, P. 115537 - 115537

Published: May 6, 2024

Language: Английский

Citations

5

Borrowing hydrogen amination: Whether a catalyst is required? DOI
Andrey S. Kozlov, Oleg I. Afanasyev, Denis Chusov

et al.

Journal of Catalysis, Journal Year: 2022, Volume and Issue: 413, P. 1070 - 1076

Published: Aug. 17, 2022

Language: Английский

Citations

19

N, S Co-Coordinated Zinc Single-Atom Catalysts for N-Alkylation of Aromatic Amines with Alcohols: The Role of S-Doping in the Reaction DOI Creative Commons
Xueping Zhang, Qiang Zhang,

Jiacheng Reng

et al.

Nanomaterials, Journal Year: 2023, Volume and Issue: 13(3), P. 445 - 445

Published: Jan. 21, 2023

S-doping emerged as a promising approach to further improve the catalytic performance of carbon-based materials for organic synthesis. Herein, facile and gram-scale strategy was developed using zeolitic imidazole frameworks (ZIFs) precursor fabrication ZIF-derived N, S co-doped carbon-supported zinc single-atom catalyst (CNS@Zn1-AA) via pyrolysis S-doped ZIF-8, which modified by aniline, ammonia thiourea prepared one-pot ball milling at room temperature. This catalyst, in Zn is dispersed single atom, displays superior activity N-alkylation hydrogen-borrowing (120 °C, turnover frequency (TOF) up 8.4 h−1). significantly enhanced CNS@Zn1-AA, it increased specific surface area defects this material simultaneously electron density sites catalyst. Furthermore, had excellent stability recyclability, no obvious loss after eight runs.

Language: Английский

Citations

12

Highly dispersed ruthenium capsulated in UiO-66-NH2 for hydrogen-borrowing-mediated N-alkylation reactions DOI
Jiahao Li,

Shiguo Ou,

Xinxin Sang

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(7), P. 1958 - 1966

Published: Jan. 1, 2024

Herein, atomically dispersed Ru sites are encapsulated within UiO-66–NH 2 frameworks to serve as a highly active, selective, and stable catalyst for amine synthesis via N -alkylation reactions of o -phenylenediamine with monohydric alcohols.

Language: Английский

Citations

4

The recyclable non-metal acid-catalyzed ammination of benzyl alcohol DOI
Ming Zhong, Min Li, Guoliang Chen

et al.

Sustainable Chemistry and Pharmacy, Journal Year: 2025, Volume and Issue: 44, P. 101957 - 101957

Published: March 3, 2025

Language: Английский

Citations

0