Switchable, Reagent-Controlled C(sp)-H Selective Iodination and Acetoxylation of 8-Methylquinolines.

J Org Chem

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, School of Foreign Languages, College of Chemistry & Materials Science, Northwest University, Xi'an 710069, P. R. China.

Published: May 2022

AI Article Synopsis

  • A new method for selectively iodinating 8-methylquinolines using an efficient Pd-catalyzed process has been developed for the first time.
  • *The technique allows for easy production of various C8-substituted quinolines, showcasing the versatility of organic iodides.
  • *By adjusting the reaction conditions, the same method can also achieve effective acetoxylation of 8-methylquinolines, with both strategies exhibiting mild conditions and good compatibility with different functional groups.

Article Abstract

An efficient Pd-catalyzed C(sp)-H selective iodination of 8-methylquinolines is reported herein for the first time. Because of the versatility of organic iodides, the method offers a facile access to various C8-substituted quinolines. By slightly switching the reaction conditions, an efficient C(sp)-H acetoxylation of 8-methylquinolines has also been enabled. Both approaches feature mild reaction conditions, good tolerance of functional groups, and a broad substrate scope.

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http://dx.doi.org/10.1021/acs.joc.2c00076DOI Listing

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