Copper‐Catalyzed Oxidative Cascade Inter‐Molecular Double Cyclization of 2‐Iodobenzamide Derivatives and Propargyl Dicarbonyl Compounds for Accessing 3‐Hydroxy‐3‐Furylisoindolinone Derivatives

Abstract

A one-pot strategy for the synthesis of 3-hydroxy-3-furylisoindolinone derivatives is reported. The reaction proceeds via a copper-catalyzed oxidative cascade inter-molecular double cyclization of 2iodobenzamide derivatives and propargyl dicarbonyl compounds in the presence of oxygen. The strategy involves several reactions including cyclization/coupling/double C(sp3)À H functionalization in a cascade manner. A wide range of 2-iodobenzamide substrates containing different substituents as well as various propargyldicarbonyl compounds and propargylsulfonyl aryl ketones can be used to access a variety of 3hydroxy-3-furylisoindolinone derivatives.

Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one

“…Most of the literature reports on these compounds involve Pd-catalyzed tandem cyclization and coupling with various coupling partners. As a part of our interest in transition metal and alkyne chemistry, our group constructs hydroxy-3-furylisoindolinone derivatives by double cyclization of 2-iodobenzamide and dicarbonyl alkyne . To the best of our knowledge, the literature has not reported the reaction of boronic acids with β-propargylic dicarbonyl compounds.…”