Highly Selective and Modular Synthesis of 3-Aryl-4-(arylethynyl)-2H-chromen-2-ones from 2-Iodoaryl 2-Arylacetates through a Carbonylative Sonogashira Coupling-Intramolecular Aldol Cascade Reaction

Chandrasekhar, Attoor ; Ramkumar, Venkatachalam ; Sankararaman, Sethuraman (2016) Highly Selective and Modular Synthesis of 3-Aryl-4-(arylethynyl)-2H-chromen-2-ones from 2-Iodoaryl 2-Arylacetates through a Carbonylative Sonogashira Coupling-Intramolecular Aldol Cascade Reaction European Journal of Organic Chemistry, 2016 (23). pp. 4041-4049. ISSN 1434-193X

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Official URL: http://doi.org/10.1002/ejoc.201600569

Related URL: http://dx.doi.org/10.1002/ejoc.201600569

Abstract

A modular method for the synthesis of 3-aryl-4-(arylethynyl)-2H-chromen-2-ones from 2-iodoaryl 2-arylacetates and arylacetylenes has been developed. The carbonylative Sonogashira coupling–intramolecular aldol casade reaction was carried out in the presence of Pd(PPh3)2(Cl)2 as the catalyst. The one-pot approach that involves the in situ formation of the 2-iodoaryl 2-arylacetates from the corresponding 2-iodophenols and 2-arylacetyl chlorides followed by the palladium-catalyzed carbonylative annulation in the presence of the arylacetylene has also been described for the formation of the 3-aryl-4-(arylethynyl)-2H-chromen-2-ones.

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