Cyclocarbonylative Sonogashira reactions of ortho-ethynylbenzamides have been investigated. The process is carried out under CO pressure, in the presence of a very small amount of PdCl2(PPh3)2 (0.4 mol %) as a catalytic precursor and without the need for a Cu salt as the co-catalyst. 2-Ethynylbenzamide reacted successfully with iodoarenes bearing electron-withdrawing and electron-donating groups, giving rise to different classes of compounds depending on the solvent used. On the contrary, N-(4- chlorophenyl)-2-ethynylbenzamide afforded exclusively polyfunctionalized isoindolinones with high stereoselectivity toward (E) isomers.

Synthesis of 3-Alkylideneisoindolin-1-ones via Sonogashira Cyclocarbonylative Reactions of 2-Ethynylbenzamides

Albano, Gianluigi;Aronica, Laura Antonella
2020-01-01

Abstract

Cyclocarbonylative Sonogashira reactions of ortho-ethynylbenzamides have been investigated. The process is carried out under CO pressure, in the presence of a very small amount of PdCl2(PPh3)2 (0.4 mol %) as a catalytic precursor and without the need for a Cu salt as the co-catalyst. 2-Ethynylbenzamide reacted successfully with iodoarenes bearing electron-withdrawing and electron-donating groups, giving rise to different classes of compounds depending on the solvent used. On the contrary, N-(4- chlorophenyl)-2-ethynylbenzamide afforded exclusively polyfunctionalized isoindolinones with high stereoselectivity toward (E) isomers.
2020
Albano, Gianluigi; Giuntini, Stefano; Aronica, Laura Antonella
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/1051107
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