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Efficient and Controllably Selective Preparation of Esters Using Uronium-Based Coupling Agents

Jean-d’Amour K. Twibanire and T. Bruce Grindley*

*Department of Chemistry, Dalhousie University, Halifax, NS, Canada B3H 4J3, Email: bruce.grindleydal.ca

J. K. Twibanire, T. B. Grindley, Org. Lett., 2011, 13, 2988-2991.

DOI: 10.1021/ol201005s (free Supporting Information)


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Abstract

Carboxylic acid esters can be prepared in very good yields at room temperature from an acid and either a phenol or an aliphatic alcohol using the peptide coupling reagents TBTU, TATU, or COMU, in the presence of organic bases. Reactions using TBTU and TATU are faster but do not occur with tertiary alcohols. Selective monoesterifications of diols and polyols can be achieved with choice of base and coupling agent.

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Key Words

Esters


ID: J54-Y2011-1670