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Intercepting Wacker intermediates with arenes: C-H functionalization and dearomatization.

ABSTRACT: An intramolecular cyclization cascade reaction has been developed utilizing a high valent palladium intermediate that generates a carbon-carbon and carbon-oxygen bond in a single transformation. This method provides rapid access to highly functionalized tricyclic scaffolds, including spirocyclic cyclohexadienones. Good yields and mild conditions are reported with high tolerance toward oxygen and water.

SUBMITTER: Matsuura BS 

PROVIDER: S-EPMC3235802 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Intercepting Wacker intermediates with arenes: C-H functionalization and dearomatization.

Matsuura Bryan S BS   Condie Allison G AG   McBee Ian A IA   Buff Ryan C RC   Karahalis Gregory J GJ   Stephenson Corey R J CR  

Organic letters 20111109 23

An intramolecular cyclization cascade reaction has been developed utilizing a high valent palladium intermediate that generates a carbon-carbon and carbon-oxygen bond in a single transformation. This method provides rapid access to highly functionalized tricyclic scaffolds, including spirocyclic cyclohexadienones. Good yields and mild conditions are reported with high tolerance toward oxygen and water. ...[more]

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