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

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-Ethynylbenzam...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 85; no. 15; pp. 10022 - 10034
Main Authors Albano, Gianluigi, Giuntini, Stefano, Aronica, Laura Antonella
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.08.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM
ISOINDOLINONE DERIVATIVES
CARBONYLATION
ARISTOLACTAMS
GLUCOSIDASE INHIBITORY-ACTIVITY
BIOLOGICAL EVALUATION
BETA-DIKETONES
3-METHYLENEISOINDOLIN-1-ONES
CYCLIZATION
ALKALOIDS
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01282