Cobalt-Catalyzed Alkylation of Nitriles with Alcohols

Singh, Arpita; Findlater, Michael

doi:10.1021/acs.organomet.1c00690

Cited by 22 publications

(10 citation statements)

References 43 publications

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“…It is important to mention that the more challenging aliphatic alcohols [15] could also be utilized in the present alkylation reaction to furnish the target molecules 3 aa – 3 af in moderate to good yields. However, methanol was found to be unsuccessful to deliver the corresponding product under optimized reaction condition which is in line with previous reports [16d,22a] …”

Section: Resultssupporting

confidence: 91%

Heteroditopic NHC Ligand Supported Manganese(I) Complexes: Synthesis, Characterization, and Activity as Non‐bifunctional Phosphine‐Free Catalyst for the α‐Alkylation of Nitriles

Donthireddy,

Rit

2023

Chemistry A European J

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In the present work, several manganese(I) complexes of chelating heteroditopic ligands Mn1‐3, featuring ImNHC (imidazol‐2‐ylidene) connected to a 1,2,3‐triazole‐N or tzNHC (1,2,3‐triazol‐5‐ylidene) donors via a methylene spacer, with possible modifications at the triazole backbone have been synthesized and completely characterized. Notably, the CO stretching frequencies, electrochemical analysis, and frontier orbital analysis certainly suggests that the chelating ImNHC‐tzNHC ligands have stronger donation capabilities than the related ImNHC‐Ntz ligand in the synthesized complexes. Moreover, these well‐defined phosphine free Mn(I)‐NHC complexes have been found to be effective non‐bifunctional catalysts for the α‐alkylation of nitriles using alcohols and importantly, the catalyst Mn1 containing ImNHC connected to a weaker triazole‐N donor displayed higher activity compared to Mn2/Mn3 containing an unsymmetrical bis‐carbene donors (ImNHC and tzNHC). A wide range of aryl nitriles were coupled with diverse (hetero)aromatic as well as aliphatic alcohols to get the corresponding products in good to excellent yields (32 examples, up to 95% yield). The detailed mechanistic studies including deuterium labelling experiments reveal that the reaction follows a Borrowing Hydrogen pathway.

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Section: Resultssupporting

confidence: 91%

Heteroditopic NHC Ligand Supported Manganese(I) Complexes: Synthesis, Characterization, and Activity as Non‐bifunctional Phosphine‐Free Catalyst for the α‐Alkylation of Nitriles

Donthireddy,

Rit

2023

Chemistry A European J

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“…The authors have cited additional references within the Supporting Information. [47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62] 100010434), fellowship code LCF/BQ/PI18/11630023. R. A. and J. R. C.-A.…”

Section: General Procedures For Materials Preparationmentioning

confidence: 99%

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

2023

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An efficient heterogeneous silver‐catalyzed α‐alkylation of nitriles and oxindoles using alcohols via borrowing hydrogen strategy has been developed for the first time. The active nanostructured material, namely [Ag/Mg4Al‐LDH], composed by silver nanoparticles (3‐4 nm average particle size) homogeneously stabilized onto a [Mg4Al‐LDH] support with suitable Brönsted basic properties, constitutes a stable catalyst for the sustainable building of novel C‐C bonds from alcohols and C‐nucleophiles. By applying this catalyst, a broad range of α‐functionalized nitriles and oxindoles has been accessed with good to excellent isolated yields and without the addition of external bases. Moreover, the novel silver nanocatalyst has also demonstrated its successful application to the cyclization of N‐[2‐(hydroxymethyl)phenyl]‐2‐phenylacetamides to afford 3‐arylquinolin‐2(1H)‐ones, through a one‐pot dehydrogenation and intramolecular α‐alkylation. Control experiments, kinetic studies and characterization data of a variety of [Ag/LDH]‐type materials confirmed the silver role in the dehydrogenation and hydrogenation steps, while [Mg4Al‐LDH] matrix is able to catalyze condensation. Interestingly, these studies suggest as key point for the successful activity of [Ag/Mg4Al‐LDH], in comparison with other [Ag/LDH]‐type nanocatalysts, the suitable acid‐base properties of this material.

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“…[10] Over the past decade, the usage of abundant base metals in place of noble metals has gained significant attention in homogeneous catalysis due to their low cost, widespread availability, and low toxicity. [11] Along this line, noteworthy progress has been witnessed in the alkylation of nitriles with Fe, [2] Co, [12] Mn, [13] and Ni [14] catalysts. In 2018, Xiao and Wang et al [2] disclosed an efficient protocol for the alkylation of aryl nitriles with a Fe-PNP pincer complex.…”

Section: Introductionmentioning

confidence: 99%

Chemoselective α‐Alkylation of Nitriles with Primary Alcohols by Manganese(I)‐Catalysis

Bera

Mukherjee

2023

Chemistry An Asian Journal

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A sustainable and easy‐to‐use protocol for the alkylation of aryl nitriles with the earth‐abundant manganese(I) catalyst is presented. The alkylation reaction employs readily available nitriles and naturally abundant alcohols as the coupling partners. The reaction proceeds chemoselectively and encompasses a broad substrate scope with good to excellent yields. The catalytic reaction yields selectively α‐branched nitriles and water as the sole byproduct. Experimental studies were executed to understand the mechanism of the catalytic reaction.

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Cobalt-Catalyzed Alkylation of Nitriles with Alcohols

Cited by 22 publications

References 43 publications

Heteroditopic NHC Ligand Supported Manganese(I) Complexes: Synthesis, Characterization, and Activity as Non‐bifunctional Phosphine‐Free Catalyst for the α‐Alkylation of Nitriles

Heteroditopic NHC Ligand Supported Manganese(I) Complexes: Synthesis, Characterization, and Activity as Non‐bifunctional Phosphine‐Free Catalyst for the α‐Alkylation of Nitriles

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

Chemoselective α‐Alkylation of Nitriles with Primary Alcohols by Manganese(I)‐Catalysis

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Cobalt-Catalyzed Alkylation of Nitriles with Alcohols

Cited by 22 publications

References 43 publications

Heteroditopic NHC Ligand Supported Manganese(I) Complexes: Synthesis, Characterization, and Activity as Non‐bifunctional Phosphine‐Free Catalyst for the α‐Alkylation of Nitriles

Heteroditopic NHC Ligand Supported Manganese(I) Complexes: Synthesis, Characterization, and Activity as Non‐bifunctional Phosphine‐Free Catalyst for the α‐Alkylation of Nitriles

Silver Supported Nanoparticles on [Mg4Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

Chemoselective α‐Alkylation of Nitriles with Primary Alcohols by Manganese(I)‐Catalysis

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Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols