Re-entry of tin in N-alkylation: first example of a homogeneous heterobimetallic Pd–Sn catalyst for base and additive free alkylation of amine and surrogates with alcohol

Mohanty, Anuradha; Roy, Sujit

doi:10.1016/j.tetlet.2016.05.018

Cited by 16 publications

(10 citation statements)

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“…The loading of the catalyst and the reaction temperature could be reduced by using a N–Heterocyclic Carbene–phosphine ligand or a benzoxazolyl ligand, thus improving the activity of the Ir catalyst. This reaction has also been reported with homogeneous Pd, using Pd(OAc) 2 , or a heterobimetallic Pd–Sn catalyst, and Rh, with the Wilkinson catalyst , . Only two examples of homogeneous non‐noble metal complexes were reported, with Cu(OAc) 2 and a NiBr 2 /phenanthroline catalytic system .…”

Section: Base Screening For the N‐alkylation Of Phenylacetamide 1a Wimentioning

confidence: 75%

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Solvent‐Free N‐Alkylation of Amides with Alcohols Catalyzed by Nickel on Silica–Alumina

et al. 2019

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The N‐alkylation of phenylacetamide with benzyl alcohol has been studied using Ni/SiO2–Al2O3. In the optimized conditions, the desired product was isolated in an excellent 98 % yield. The reaction could advantageously be performed in neat conditions, with a slight excess of amide and a catalytic amount of base. These conditions were tested on a large range of amides and alcohols, affording 24 compounds in 13 to 99 % isolated yields.

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Section: Base Screening For the N‐alkylation Of Phenylacetamide 1a Wimentioning

confidence: 75%

“…Pd-Sn catalyst, [26] and Rh, with the Wilkinson catalyst. [27,28] Only two examples of homogeneous non-noble metal complexes were reported, with Cu(OAc) 2 [29] and a NiBr 2 /phenanthroline catalytic system.…”

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confidence: 99%

Solvent‐Free N‐Alkylation of Amides with Alcohols Catalyzed by Nickel on Silica–Alumina

et al. 2019

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“…Catalyst structures are provided both in the SI and herein below (see Figures , , , and ). The catalysts of this group are discussed in refs − .…”

Section: Borrowing Hydrogen Amination Of Benzyl Alcohol By Anilinementioning

confidence: 99%

Borrowing Hydrogen Amination Reactions: A Complex Analysis of Trends and Correlations of the Various Reaction Parameters

et al. 2022

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Borrowing hydrogen or the hydrogen autotransfer amination is a powerful approach to create single C–N bonds, starting from stable and readily available substrates: amines and alcohols. It is considered as one of the most atom-efficient and green methods to synthesize complex amines. Herein, we attempted to arrange the array of the existing data in a comprehensive and structured manner and determine correlations between the experimental conditions and catalysis outcome both within different groups of catalysts and between the defined groups using the machine analysis. For each type of N-nucleophiles (aromatic, aliphatic, and heteroaromatic amines, amides), the most efficient working conditions were suggested, including attributing the optimal base and temperature regime for each metal.

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“…N-containing compounds, [1] are used as basic intermediates in dyes, [2] herbicides, [3] industrial chemicals, [4] insecticides, agrochemical, [5] functional materials, [6] pharmaceuticals, [7] and in various bioactive molecules. [8,9] Thus, N-alkylation is an important class of synthetic reaction.…”

Section: Introductionmentioning

confidence: 99%

An overview of iron‐catalyzed N‐alkylation reactions

Stiniya

Saranya

Anilkumar

2021

Applied Organom Chemis

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N‐containing compounds are very important molecules in nature and in the field of synthetic organic chemistry. N‐alkylation reactions play crucial role in the area of pharmaceuticals and various other industrial chemical syntheses. Iron‐catalyzed N‐alkylation reactions have attained greater acceptance among the scientific community. Environmentally benign, abundant, nontoxic, biocompatible, reusable, and inexpensive iron catalysts are gaining more attention in various research fields. Green protocols, milder reaction conditions, wide substrate scope, and so forth, signify the prominent nature of iron‐catalyzed N‐alkylation reactions. Most of the protocols are eco‐friendly and atom economic since water is the only by‐product. This review gives an overview of the advances in the Fe‐catalyzed N‐alkylation reactions covering literature up to 2021.

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Re-entry of tin in N-alkylation: first example of a homogeneous heterobimetallic Pd–Sn catalyst for base and additive free alkylation of amine and surrogates with alcohol

Cited by 16 publications

References 50 publications

Solvent‐Free N‐Alkylation of Amides with Alcohols Catalyzed by Nickel on Silica–Alumina

Solvent‐Free N‐Alkylation of Amides with Alcohols Catalyzed by Nickel on Silica–Alumina

Borrowing Hydrogen Amination Reactions: A Complex Analysis of Trends and Correlations of the Various Reaction Parameters

An overview of iron‐catalyzed N‐alkylation reactions

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