Iron-catalyzed remote C-H alkylation of 8-amidoquinolines with cycloalkanes

• Main Authors: Xu, Wengang, Wu, Mingbo, Yoshikai, Naohiko
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2022
• Subjects: Science::Chemistry; Iron Catalysis; Quinolines
• Online Access: https://hdl.handle.net/10356/161424
• Institution: Nanyang Technological University

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.