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Relevant academic research and scientific papers

Zwitterionic-surfactant-stabilized palladium nanoparticles as catalysts in the hydrogen transfer reductive amination of benzaldehydes

Palladium nanoparticles (NPs) stabilized by a zwitterionic surfactant are revealed here to be good catalysts for the reductive amination of benzaldehydes using formate salts as hydrogen donors in aqueous isopropanol. In terms of environmental impact and e

Easy Access to Versatile Catalytic Systems for C?H Activation and Reductive Amination Based on Tetrahydrofluorenyl Rhodium(III) Complexes

On the basis of the 1,2,3,4-tetrahydrofluorenyl ligand, a simple approach was developed to new effective rhodium catalysts for the construction of C?C and C?N bonds. The halide compounds [(η5-tetrahydrofluorenyl)RhX2]2 (2

Thiourea-Catalyzed C?F Bond Activation: Amination of Benzylic Fluorides

We describe the first thiourea-catalyzed C?F bond activation. The use of a thiourea catalyst and Ti(OiPr)4 as a fluoride scavenger allows the amination of benzylic fluorides to proceed in moderate to excellent yields. Preliminary results with S- and O-based nucleophiles are also presented. DFT calculations reveal the importance of hydrogen bonds between the catalyst and the fluorine atom of the substrate to lower the activation energy during the transition state.

Hydrazone complexes of ruthenium(II): Synthesis, crystal structures and catalytic applications in N-alkylation reactions

A series of new Ru(II) complexes of 8-hydroxy quinoline-2-carboxyaldehyde hydrazone of the general formula [RuH(CO)(EPh3)2L] (1–6) (E = P or As, L = N’-((8-hydroxyquinolin-2-yl)methylene)thiophene-2-carbohydrazide (HQ-THy), N’-((8-hydroxyquinolin-2-yl)methylene)isonicotinohydrazide (HQ-IHy), N’-((8-hydroxyquinolin-2-yl)methylene) benzohydrazide (HQ-BHy)) have been synthesized. They have been characterized by elemental analysis, IR, NMR (1H, 13C & 31P) and ESI-MS spectral methods. Further, structures of two of the complexes have been determined by single crystal X-ray diffraction technique which revealed a pseudo octahedral geometry with the coordination of the quinoline nitrogen and quinoline oxygen atoms of the ligand. All the new complexes have been employed as efficient catalysts in N-alkylation reactions for the synthesis of tertiary amines by the coupling of secondary amines with aromatic primary alcohols at low catalyst loading with maximum yields. In addition, the effects of substituents on the ligands, different solvents as well as bases and amounts of catalyst loading on the catalytic activity of the complexes have been thoroughly investigated. Complex 1 was found to be efficient catalyst towards N-alkylation of alcohols with the amine. Further, a variety of secondary amines and aromatic (hetero) primary alcohols with various functional groups have also been successfully used in the N-alkylation reactions and it has been found that only one equivalent of the alcohol was consumed in the process.

Tris(pyrazolyl)borate rhodium complexes. Application for reductive amination and esterification of aldehydes in the presence of carbon monoxide

The halide complexes TpRhCl2(MeOH) and TpMe2RhI2(CO) (Tp = hydrotris-(pyrazolyl)borate; TpMe2 = hydrotris-(3,5-dimethylpyrazolyl)borate) were synthesized by reactions of RhCl3 with K[Tp] in methanol and TpMe2Rh(CO)2 with iodine, respectively. Reactions of TpMe2RhCl2(MeOH) and TpMe2RhI2(CO) with 1,10-phenanthroline afford the phenanthroline derivatives [TpMe2Rh(phen)X]+ (X = Cl, I). The structures of TpRhCl2(MeOH) and TpRhI2(CO) were determined by X-ray diffraction. Tris(pyrazolyl)borate rhodium complexes effectively catalyze the reductive amination and the reductive esterification of aldehydes in the presence of carbon monoxide.

Photochemical benzylic bromination in continuous flow using BrCCl3 and its application to telescoped p-methoxybenzyl protection

BrCCl3 represents a rarely used benzylic brominating reagent with complementary reactivity to other reagents. Its reactivity has been revisited in continuous flow, revealing compatibility with electron-rich aromatic substrates. This has brought about the development of a p-methoxybenzyl bromide generator for PMB protection, which was successfully demonstrated on a pharmaceutically relevant intermediate on 11 g scale, giving 91% yield and a PMB-Br space-time-yield of 1.27 kg L?1 h?1

Anthracene-rhodium complexes with metal coordination at the central ring-a new class of catalysts for reductive amination

A new class of anthracene complexes with a metal coordinated at the central ring was applied in catalysis for the first time. As a result, a simple and efficient protocol for reductive amination that involves CO as a reducing agent has been developed. The rhodium complex [(cyclooctadiene)Rh(C10H4Me2(OMe)4)]+ (1 mol%) catalyses such reactions under mild conditions (40-130 °C) and produces a variety of amines in good yields (74-95%) without affecting the functional groups. The protocol is acceptable for all combinations of aldehydes (aromatic and aliphatic), ketones (aromatic and aliphatic) and amines (aromatic and aliphatic; primary and secondary).

Alkylation of cyclic amines with alcohols catalyzed by Ru(II) complexes bearing N-Heterocyclic carbenes

This paper includes the synthesis of 2-(1,3-dioxane-2-yl)ethyl substituted benzimidazole substituted N-heterocyclic carbenes precursors and their ruthenium complexes. Synthesized compounds were characterized by elemental analysis and NMR spectroscopy. All complexes have been tested in the alkylation of pyrrolidine and morpholine with alcohols, showing an excellent activity in this reaction.

Cobalt-Rhodium Heterobimetallic Nanoparticle-Catalyzed N-Alkylation of Amines with Alcohols to Secondary and Tertiary Amines

Without the requirement for base or other additives, Co2Rh2/C can selectively catalyze both mono- and bis-N-alkylation through the coupling of simple alcohols with amines, yielding a range of secondary and tertiary amines in good to excellent isolated yields. The reaction can be applied to benzyl alcohol with optically active 1-phenylethan-1-amines, and secondary amines were isolated in quantitative yields with an excellent enantiomeric excess (ee > 94%). Selectivity is achieved by varying the reaction temperature and amount of catalyst used. This catalytic system has several advantages including eco-friendliness and a simple workup procedure. The catalyst can be successfully recovered and reused ten times without any significant loss of activity.

Indenyl rhodium complexes. Synthesis and catalytic activity in reductive amination using carbon monoxide as a reducing agent

Indenyl-ligated rhodium(III) catalyst [(η5-indenyl)RhX2]n (1) is reported for the synthesis of alkylated amines via catalytic reductive amination using carbon monoxide as a reducing agent. Water as a solvent was found to b