1. Synthesis of 3-Alkylideneisoindolin-1-ones via Sonogashira Cyclocarbonylative Reactions of 2-Ethynylbenzamides
- Author
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Gianluigi Albano, Stefano Giuntini, and Laura Antonella Aronica
- Subjects
010405 organic chemistry ,Chemistry ,Organic Chemistry ,Sonogashira coupling ,isoindolinone ,010402 general chemistry ,solvent ,01 natural sciences ,Combinatorial chemistry ,Article ,0104 chemical sciences ,Cyclocarbonylation ,Scientific method ,Cyclocarbonylation, Sonogashira reaction, isoindolinone, solvent ,Sonogashira reaction - 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.
- Published
- 2020