The palladium-catalyzed hydroarylation and hydrovinylation of tertiary 3-(o-acetoxyaryl)- and 3-(o-benzoyloxyaryl)propynols - A route to 4-aryl- and 4-vinyl-2,2-dimethyl-3-chromenes

Citation
A. Arcadi et al., The palladium-catalyzed hydroarylation and hydrovinylation of tertiary 3-(o-acetoxyaryl)- and 3-(o-benzoyloxyaryl)propynols - A route to 4-aryl- and 4-vinyl-2,2-dimethyl-3-chromenes, EUR J ORG C, (24), 2000, pp. 4099-4108
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
24
Year of publication
2000
Pages
4099 - 4108
Database
ISI
SICI code
1434-193X(200012):24<4099:TPHAHO>2.0.ZU;2-3
Abstract
The palladium-catalyzed hydroarylation and hydrovinylation of tertiary 3-(o -acetoxyaryl)- and 3-(o-benzoyloxyaryl) propynols provides a regio- and ste reoselective route to allylic alcohols with aryl and vinyl substituents whi ch can be readily converted into the corresponding chromene derivatives. Th e hydroarylation and hydrovinylation reaction is believed to proceed throug h a carbopalladation step whose regiochemistry is primarily controlled by t he directing effect of the tertiary hydroxy group.