Tandem Rh(III)-Catalyzed Oxidative Acylation of Secondary Benzamides with Aldehydes and Intramolecular Cyclization: The Direct Synthesis of 3-Hydroxyisoindolin-1-ones

The rhodium-catalyzed oxidative acylation between secondary benzamides and aryl aldehydes via sp2 C–H bond activation followed by an intramolecular cyclization is described. This method results in the direct and efficient synthesis of 3-hydroxyisoindolin-1-one building blocks.

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Bibliographic Details
Published in:Organic letters 2012-02, Vol.14 (3), p.906-909
Main Authors: Sharma, Satyasheel, Park, Eonjeong, Park, Jihye, Kim, In Su
Format: Article
Language:English
Subjects:
Acylation
Aldehydes - chemistry
Benzamides - chemistry
Catalysis
Cyclization
Hydroxylation
Indoles - chemical synthesis
Molecular Structure
Oxidation-Reduction
Rhodium - chemistry
Stereoisomerism
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Description
Summary:The rhodium-catalyzed oxidative acylation between secondary benzamides and aryl aldehydes via sp2 C–H bond activation followed by an intramolecular cyclization is described. This method results in the direct and efficient synthesis of 3-hydroxyisoindolin-1-one building blocks.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2034228