Iron-Catalyzed Remote C–H Alkylation of 8-Amidoquinolines with Cycloalkanes

Abstract

An iron-catalyzed, peroxide-mediated cross-dehydrogenative coupling between 8-amidoquinolines and cycloalkanes has been developed for the site-selective alkylation of the quinoline nucleus at the C5 position. The reaction tolerates various substituted N-(quinolin-8-yl)benzamides and N-(quinolin-8-yl)alkylamides, affording the corresponding C5-alkylation products in good yields. On the basis of control experiments, a reaction mechanism involving the addition of an alkyl radical to an iron-chelated intermediate is proposed.

Key words

C–H functionalization - iron catalysis - quinolines - alkyl­ation - radical reaction

Publication History

Received: 20 November 2020

Accepted after revision: 15 December 2020

Accepted Manuscript online:
15 December 2020

Article published online:
20 January 2021

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