Friedel–Crafts alkylation of indoles with β-nitroalkenes using ammonium niobium oxalate as a recyclable catalyst

Deepak, Rajasekharan Jayakumari; Sathishkumar, Pushpanathan N.; Karvembu, Ramasamy

doi:10.1039/d2nj04542g

New J. Chem.

2022

DOI: 10.1039/d2nj04542g

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Friedel–Crafts alkylation of indoles with β-nitroalkenes using ammonium niobium oxalate as a recyclable catalyst

Rajasekharan Jayakumari Deepak

Pushpanathan N. Sathishkumar

Ramasamy Karvembu

Abstract: An environmentally benign method has been developed for the Friedel-Crafts alkylation of indoles with nitroalkenes using ammonium niobium oxalate (ANO) as a recyclable catalyst. The reactions were carried out under...

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Cited by 3 publications

References 60 publications

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Solvent Dependent Selectivity in the Synthesis of 1,2‐Disubstituted and 2‐Substituted Benzimidazoles by Dehydrogenative Coupling Reactions with Ruthenium‐Polyoxoniobate Catalysts

Deepak,

N. E.,

Karvembu

2024

Asian J Org Chem

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Ruthenium‐polyoxoniobate complexes were found to be efficient catalysts for the selective synthesis of 2‐substituted benzimidazoles and 1,2‐disubstituted benzimidazoles by solvent switching. The current strategy enables the synthesis of 2‐substituted benzimidazoles in water as a green solvent. Switching to aprotic solvents resulted in the formation of 1,2‐disubstituted benzimidazoles as the major product. Control experiments showed the involvement of both acceptorless dehydrogenative and oxidative coupling pathways. The method was extended to synthesize various 2‐substituted and 1,2‐disubstituted benzimidazole derivatives, and the desired products were obtained in moderate to good yields.

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Solvent Dependent Selectivity in the Synthesis of 1,2‐Disubstituted and 2‐Substituted Benzimidazoles by Dehydrogenative Coupling Reactions with Ruthenium‐Polyoxoniobate Catalysts

Deepak,

N. E.,

Karvembu

2024

Asian J Org Chem

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ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles

Dapper,

Mena,

Silva

et al. 2025

Tetrahedron Green Chem

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Fe(II)-Catalyzed Metal–Ligand Cooperative Approach for Selective C3-Alkylation of Indoles

Mandal,

Paul,

Chakraborty

2024

Synlett

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Herein, we report a straightforward approach for synthesizing C3-alkylated indoles selectively via an iron-catalyzed alkylation of indoles using alcohols as the alkylating agents. A well-defined, air-stable, and easy-to-prepare Fe(II)-catalyst of a redox-active tridentate arylazo scaffold was used as a catalyst. Various C3-alkylated indoles were prepared selectively in moderate to good isolated yields by coupling indoles with different substituted alcohols. The methodology is compatible with the gram-scale synthesis. Control experiments were performed to unveil the mechanism, which revealed that the alkylation reaction proceeds via borrowing hydrogen pathway where the coordinated azo-aromatic ligand actively participates during catalysis, acting as an electron and hydrogen reservoir.

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Friedel–Crafts alkylation of indoles with β-nitroalkenes using ammonium niobium oxalate as a recyclable catalyst

Abstract: An environmentally benign method has been developed for the Friedel-Crafts alkylation of indoles with nitroalkenes using ammonium niobium oxalate (ANO) as a recyclable catalyst. The reactions were carried out under...

Cited by 3 publications

References 60 publications

Solvent Dependent Selectivity in the Synthesis of 1,2‐Disubstituted and 2‐Substituted Benzimidazoles by Dehydrogenative Coupling Reactions with Ruthenium‐Polyoxoniobate Catalysts

Solvent Dependent Selectivity in the Synthesis of 1,2‐Disubstituted and 2‐Substituted Benzimidazoles by Dehydrogenative Coupling Reactions with Ruthenium‐Polyoxoniobate Catalysts

ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles

Fe(II)-Catalyzed Metal–Ligand Cooperative Approach for Selective C3-Alkylation of Indoles

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