Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes

The palladium/Lewis acid cocatalyzed ring-opening reaction of various C -substituted unsymmetrical oxabenzonorbornadienes (OBD) with oxime nucleophiles was investigated. The effects of various C substituents were explored. Moderate to excellent yields and excellent regioselectivities were obtained f...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-06, Vol.84 (12), p.8309-8314
Main Authors: Hill, Jarvis, Tam, William
Format: Article
Language:English
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Summary:The palladium/Lewis acid cocatalyzed ring-opening reaction of various C -substituted unsymmetrical oxabenzonorbornadienes (OBD) with oxime nucleophiles was investigated. The effects of various C substituents were explored. Moderate to excellent yields and excellent regioselectivities were obtained for electron-withdrawing groups. The presence of electron-donating alkyl groups leads to isomerization of the corresponding OBD to afford the substituted naphthol derivatives. Additionally, a mechanism for the formation of C regioisomeric ring-opened products has been proposed.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01094