Metal- and Solvent-Free Synthesis of m-Terphenyls by an Iodine-Catalyzed Tandem Formal [3+3]-Cycloaddition/Oxidation

Abstract

A tandem formal [3+3]-cycloaddition/oxidation between chalcones and β-enamine esters, employing iodine as a catalyst, was developed for the construction of various substituted m-terphenyls. A wide range of chalcones and β-enamine esters were tested under metal- and solvent-free conditions for the synthesis of substituted m-terphenyls in good to excellent yields in the presence of sulfur as an oxidant. This reaction proceeds with the formation of four new bonds and one new ring, with a high atom economy.

Key words

terphenyls - chalcones - enamine esters - cycloaddition - iodine catalysis - oxidation

Publication History

Received: 13 May 2022

Accepted after revision: 19 July 2022

Accepted Manuscript online:
19 July 2022

Article published online:
11 August 2022

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