Sulfolane Mediated Highly Selective Synthesis of Mono and Bis-aryl-2-Methyl-6- Fluoro-Indoles and Their Halogenated Synthons

Koppada    Masthan    Raju; Ravi    Kumar    Cheedarala; Arumugam       Pandurangan

doi:10.2174/1385272824999200914111909

Abstract

A simple, efficient, and cheap strategy has been developed for N-arylation of indoles with hexafloro benzene (1) via incorporating sulfolane as an eco-friendly solvent. NMonopentafluoroarylindole (3) at ambient conditions and N, N-bistetrafluoroaryl indole (4) at elevated temperatures were conveniently obtained by simple nucleophilic substitution using NaOH as the base and sulfolane as a reaction medium to obtain in moderately good yields, respectively. Subsequently, 3-chloro, 3-bromo, and 3-iodomono-pentafluoroarylindoles and 3, 3’-dichloro, 3, 3’-dibromo and 3, 3’-diIodobistetrafluoroaryl indoles were prepared in good yields by using respective halogenating reagents and solvents. All the chemical transformations were confirmed by analytical tools such as 1HNMR, FR-IR and HRMS analysis.

Keywords: 2-Methyl-6-fluoro-indole, hexafluorobezene, indole derivative, mono fluoroaryl indoles and bisfluoroaryl indoles, nucleophilic substitution, 1HNMR.

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DOI https://dx.doi.org/10.2174/1385272824999200914111909	Print ISSN 1385-2728
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Current Organic Chemistry

Sulfolane Mediated Highly Selective Synthesis of Mono and Bis-aryl-2-Methyl-6- Fluoro-Indoles and Their Halogenated Synthons

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Catalytic C-H bond activation as a tool for functionalization of heterocycles

Current Organic Chemistry

Sulfolane Mediated Highly Selective Synthesis of Mono and Bis-aryl-2-Methyl-6- Fluoro-Indoles and Their Halogenated Synthons

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Catalytic C-H bond activation as a tool for functionalization of heterocycles

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