Synlett 2023; 34(07): 807-814
DOI: 10.1055/a-1903-5174
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Chemical Synthesis and Catalysis in India

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

Thangavel Pavithra
a   Department of Chemistry, School of Chemical and Biotechnology, SASTRA Deemed University, Thanjavur-613401, India
,
Gnanaoli Karthiyayini
a   Department of Chemistry, School of Chemical and Biotechnology, SASTRA Deemed University, Thanjavur-613401, India
,
Subbiah Nagarajan
b   Department of Chemistry, National Institute of Technology-Warangal, Warangal-506004, India
,
Vellaisamy Sridharan
c   Department of Chemistry and Chemical Sciences, Central University of Jammu, Rahya-Suchani (Bagla), District-Samba, Jammu-181143, Jammu and Kashmir, India
,
C. Uma Maheswari
a   Department of Chemistry, School of Chemical and Biotechnology, SASTRA Deemed University, Thanjavur-613401, India
› Author Affiliations
Financial support from the Science and Engineering Research Board (SERB) through the award of a research grant (CRG/2021/006424) is gratefully acknowledged.


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.

Supporting Information



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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