Transition-Metal-Free Acylation of Quinolines and Isoquinolines with Arylmethanols via Oxidative Cross-Dehydrogenative Coupling Reactions

Abstract

An efficient acylation of quinolines and isoquinolines is described by use of arylmethanols as the acylating agents through a C-C bond formation via an oxidative cross-dehydrogenative coupling (CDC) strategy. This C-aroylation reaction was carried out by use of K 2 S 2 O 8 as oxidant and methyltrioctylammonium chloride (Aliquat 336) as a transfer agent in MeCN at 80 °C under transition-metal-free conditions.

Regio‐ and Diastereoselective KMnO4/RCO2H Mediated Acyloxyarylation of Chalcones – An Indirect α‐Arylation of Chalcones

“…Despite great achievements, it is still of importance to develop novel and efficient methods for the preparation of organic compounds from readily available starting materials. In continuation of our recent efforts, herein, we report regio‐ and diastereoselective acyloxyarylation of chalcones using arylboronic acids as aryl source and carboxylic acids as acyloxyl source by KMnO 4 as oxidant which led to a useful approach for the β‐acyloxylation and α‐arylation of chalcones (Scheme ).…”

Visible-Light-Mediated Oxidation of 1-Benzyl-3,4-dihydroisoquinolines with Dioxygen: A Switchable Synthesis of 1-Benzoylisoquinolines and 1-Benzoyl-3,4-dihydroisoquinolines

“…4,5 However, literature methods for the preparation of 1-benzoyl-6,7-dialkoxyisoquinolines remain rare. 2f 4b 4d 5c…”

Recent Developments in Transition Metal‐Free Cross‐Dehydrogenative Coupling Reactions for C–C Bond Formation

“…A metal‐free approach for the synthesis of 1‐aroyl quinoline has been described by Adib et al [ 42 ] The coupling of quinolines and isoquinolines with aryl methanols as acylating agents in presence of K 2 S 2 O 8 /Aliquat 336 system in acetonitrile as solvent at 80 °C afforded the coupled products in good yield (Scheme 53).…”