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Easily Prepared Azopyridines As Potent and Recyclable Reagents for Facile Esterification Reactions. An Efficient Modified Mitsunobu Reaction

Nasser Iranpoor*, Habib Firouzabadi*, Dariush Khalili and Somayeh Motevalli

*Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran, Email: iranpoorchem.susc.ac.ir, firouzabadichem.susc.ac.ir

N. Iranpoor, H. Firouzabadi, D. Khalili, S. Motevalli, J. Org. Chem., 2008, 73, 4882-4887.

DOI: 10.1021/jo8000782 (free Supporting Information)


Abstract

4,4′-azopyridine is a suitable electron-deficient reagent for Mitsunobu esterification and thioesterification reactions. This new reagent facilitates the isolation of its hydrazine byproduct without restricting the reaction scope. The pyridine hydrazine byproduct can be simply reoxidized. The stereochemistry of the reaction under the reported conditions is with perfect retention of configuration.

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proposed mechanism



Key Words

Esters, Thioesters, Mitsunobu Reaction


ID: J42-Y2008-1700