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

Author:

Raju Koppada Masthan1,Cheedarala Ravi Kumar2,Pandurangan Arumugam1

Affiliation:

1. Department of Chemistry, Anna University, Guindy, Chennai, Tamil Nadu, India

2. Department of Materials Science and Engineering, Ulsan National Institute of Science and Technology (UNIST), UNIST-Gil, Ulsan, Korea

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. N-Monopentafluoroarylindole (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.

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry

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