Catalyst- and Additive-Free Synthesis of Fluoroalkoxyquinolines

Abstract

A nucleophilic substitution approach has been developed for the synthesis of C4 fluoroalkoxyquinolines from 4-haloquinolines by utilizing hexafluoro-2-propanol and trifluoroethanol as nucleophiles. The method is also applicable for 2-chloroquinolines, 1-chloroisoquinoline, and 2-chlorobenzimidazole. Control experiments revealed that substitution occurs only at the C2 and C4 positions of quinolines.

Key words

4-chloroquinoline - 2-chloroquinoline - 1-chloroisoquinoline - HFIP - fluoroalkoxylation

Publication History

Received: 12 May 2021

Accepted after revision: 17 June 2021

Accepted Manuscript online:
17 June 2021

Article published online:
20 July 2021

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