Masked Formylation with 2-Benzotriazolyl-1,3-dioxolane, a Novel Formyl Cation Equivalent

Alan R. Katritzky*, Herman H. Odens and Michael V. Voronkov

*Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, Gainesville, Florida 32611-7200

A. R. Katritzky, H. H. Odens, M. V. Voronkov, J. Org. Chem., 2000, 65, 1886-1888.

DOI: 10.1021/jo991624u

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Abstract

A benzotriazole reagent derived from 2-ethoxydioxolane and benzotriazole can be used as a remarkably stable and versatile electrophilic formylating reagent in reactions with Grignard reagents and organozinc reagents. The procedure is mild, efficient, and tolerable to multifunctional organic molecules, which makes it suitable for multistep syntheses.

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Key Words

formylation, protected carbonyl compounds, 1,3-dioxolanes

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ID: J42-Y2000