Mild and efficient deprotection of allyl ethers of phenols and hydroxycoumarins using a palladium on charcoal catalyst and ammonium formate

Tetrahedron Letters

Volumn 47, Issue 32, 2006, Pages 5807-5810

  Ganguly, Nemai C ^a   Dutta, Sanjoy ^a   Datta, Mrityunjoy ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

Allyl coumarinyl ether; Allyl phenyl ether; Deallylation; Pd C and ammonium formate

Indexed keywords

ALCOHOL; ALLYL ETHER; AMMONIUM FORMATE; CHARCOAL; COUMARIN; ETHER; HYDROXYCOUMARIN; PALLADIUM; PHENOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DEPROTECTION REACTION;

EID: 33745610023     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.176     Document Type: Article

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39. The current deallylation may be an isomerization-hydrolysis sequence with ammonium formate acting as a mild hydrolytic cleaving agent for acid labile enol ethers generated by isomerization of allyl ethers with Pd/C. However, insertion of palladium between the C-O bond by oxidative addition and removal of ArO from the resulting π-allyl palladium complex by nucleophilic attack of formate is an equally possible mechanistic route.