Metal-free synthesis of selenoesters directly from carboxylic acids using bifunctional selenoureas under batch and continuous-flow conditions

Mhate, Mouzma; Mahanta, Chandra Sekhara; Dhaked, Devendra K.; Ravichandiran, Velyutham; Swain, Sharada Prasanna

doi:10.1039/d3cc02872k

Chem. Commun.

2023

DOI: 10.1039/d3cc02872k

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Metal-free synthesis of selenoesters directly from carboxylic acids using bifunctional selenoureas under batch and continuous-flow conditions

Mouzma Mhate,

Chandra Sekhara Mahanta,

Devendra K. Dhaked

et al.

Abstract: A new metal-free method for the synthesis of selenoesters directly from carboxylic acids in a flow reactor is reported. The carboxylic acids, Michael acceptors, bifunctional selenoureas (source of selenium and...

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Cited by 6 publications

References 45 publications

(42 reference statements)

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CuBr2/1,10-phenanthroline-catalyzed benzylic oxidation via a bromo intermediate for the synthesis of α-keto esters under continuous-flow conditions

Jethy,

Mhate,

Kumar

et al. 2024

Molecular Catalysis

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CuBr2/1,10-phenanthroline-catalyzed benzylic oxidation via a bromo intermediate for the synthesis of α-keto esters under continuous-flow conditions

Jethy,

Mhate,

Kumar

et al. 2024

Molecular Catalysis

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Metal-Free Synthesis of Pharmaceutically Relevant Sulfonylureas via Direct Reaction of Sulfonamides with Amides

Mondal,

Sati,

Hashim

et al. 2024

J. Org. Chem.

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A metal-free process has been developed for the sustainable synthesis of medicinally important sulfonylureas in one pot via the direct reaction of sulfonamides with amides in green solvent (DMC). The reaction proceeded efficiently at room temperature, and the products were obtained in good to excellent yields. The use of readily accessible, inexpensive, and environmentally benign starting materials and reagents, metal-free mild reaction conditions, wide substrate scope, tolerance to air and moisture, operational simplicity, and good atom economy are the salient features of this reaction protocol. Gram-scale synthesis of antidiabetic drugs tolbutamide and chlorpropamide in excellent yields further revealed the practical utility of this procedure. Additionally, the synthetic value of this straightforward method is showcased by the late-stage modification of drug molecules, including drug−drug conjugation with good yields. Preliminary mechanistic studies indicated the in situ generation of an isocyanate intermediate, which further reacts with sulfonamide to form sulfonylurea. As compared to other related methods reported for sulfonylurea synthesis, the current method obviates the requirement of traditional multistep protocols involving isolation of hazardous isocyanates and avoids the use of toxic phosgene.

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A copper(ii) bromide/NMO system for α-amination of esters under continuous-flow conditions with reduced catalyst loading

Chauhan,

Kumar,

Ravichandiran

et al. 2024

New J. Chem.

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Metal-free synthesis of selenoesters directly from carboxylic acids using bifunctional selenoureas under batch and continuous-flow conditions

Abstract: A new metal-free method for the synthesis of selenoesters directly from carboxylic acids in a flow reactor is reported. The carboxylic acids, Michael acceptors, bifunctional selenoureas (source of selenium and...

Cited by 6 publications

References 45 publications

CuBr2/1,10-phenanthroline-catalyzed benzylic oxidation via a bromo intermediate for the synthesis of α-keto esters under continuous-flow conditions

CuBr2/1,10-phenanthroline-catalyzed benzylic oxidation via a bromo intermediate for the synthesis of α-keto esters under continuous-flow conditions

Metal-Free Synthesis of Pharmaceutically Relevant Sulfonylureas via Direct Reaction of Sulfonamides with Amides

A copper(ii) bromide/NMO system for α-amination of esters under continuous-flow conditions with reduced catalyst loading

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