Tandem Rh(III)-catalyzed oxidative acylation of secondary benzamides with aldehydes and intramolecular cyclization: the direct synthesis of 3-hydroxyisoindolin-1-ones

Satyasheel Sharma; Eonjeong Park; Jihye Park; In Su Kim

doi:10.1021/ol2034228

Tandem Rh(III)-catalyzed oxidative acylation of secondary benzamides with aldehydes and intramolecular cyclization: the direct synthesis of 3-hydroxyisoindolin-1-ones

Org Lett. 2012 Feb 3;14(3):906-9. doi: 10.1021/ol2034228. Epub 2012 Jan 20.

Authors

Satyasheel Sharma¹, Eonjeong Park, Jihye Park, In Su Kim

Affiliation

¹ Department of Chemistry, University of Ulsan, Ulsan, 680-749, Republic of Korea.

PMID: 22263914
DOI: 10.1021/ol2034228

Abstract

The rhodium-catalyzed oxidative acylation between secondary benzamides and aryl aldehydes via sp(2) 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acylation
Aldehydes / chemistry*
Benzamides / chemistry*
Catalysis
Cyclization
Hydroxylation
Indoles / chemical synthesis*
Molecular Structure
Oxidation-Reduction
Rhodium / chemistry*
Stereoisomerism

Substances

Aldehydes
Benzamides
Indoles
indoline
Rhodium