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

Wengang Xu; Mingbo Wu; Naohiko Yoshikai

doi:10.1055/a-1337-5416

Synthesis, Table of Contents

Synthesis 2021; 53(17): 3144-3150
DOI: 10.1055/a-1337-5416

special topic

Bond Activation – in Honor of Prof. Shinji Murai

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

Wengang Xu

^aCollege of New Energy, Institute of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), Qingdao 266580, P. R. of China

,

Mingbo Wu∗

^aCollege of New Energy, Institute of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), Qingdao 266580, P. R. of China

,

Naohiko Yoshikai ∗

^bDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

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Abstract

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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

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References

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