Radical-Induced Cascade Annulation/Hydrocarbonylation for Construction of 2-Aryl-4H-chromen-4-ones

A robust metal- and solvent-free cascade radical-induced C-N cleavage/intramolecular 6-endo-dig annulation/hydrocarbonylation for the synthesis of the valuable 2-aryl-4H-chromen-4-ones is described. This practical synthesis strategy utilizes propargylamines and air as the oxygen source and green car...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-11, Vol.27 (21), p.7412
Main Authors: He, Xinwei, Xu, Keke, Liu, Yanan, Wang, Demao, Tang, Qiang, Hui, Wenjie, Chen, Haoyu, Shang, Yongjia
Format: Article
Language:English
Subjects:
Activated carbon
Adaptability
Aromatic compounds
Carbonyls
cascade reaction
Chemical reactions
chromen-4-ones
Experiments
Functional groups
hydrocarbonylation
Organic chemistry
propargylamines
Protocol
Reagents
Solvents
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Summary:A robust metal- and solvent-free cascade radical-induced C-N cleavage/intramolecular 6-endo-dig annulation/hydrocarbonylation for the synthesis of the valuable 2-aryl-4H-chromen-4-ones is described. This practical synthesis strategy utilizes propargylamines and air as the oxygen source and green carbonylation reagent, in which propargylamines are activated by the inexpensive and available dimethyl 2,2′-azobis(2-methylpropionate) (AIBME) and (PhSe)2 as the radical initiators. This simple and green protocol features wide substrate adaptability, good functional group tolerance, and amenability to scaling up and derivatizations.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27217412