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General Transition Metal-Free Synthesis of NH-Pyrroles from Secondary Alcohols and 2-Aminoalcohols

Besir Krasniqi, Kayle Geerts, Wim Dehaen*

*Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven 3000, Belgium, Email: wim.dehaenkuleuven.be

J.-A.  Shin, J. Kim, H. Lee, S. Ha, H.-Y. Lee, J. Org. Chem., 2019, 84, 4558-4565.

DOI: 10.1021/acs.joc.8b03215 (free Supporting Information)


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Abstract

A transition metal-free one-pot reaction of secondary alcohols and 2-aminoalcohols provides various substituted NH-pyrroles via an Oppenauer oxidation in the presence of benzophenone as an inexpensive reagent. The oxidation of the secondary alcohols under mild condition to ketones is followed by an in situ condensation with aminoalcohol, and oxidative cyclization to the target pyrrole ring.


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Key Words

pyrroles, Oppenauer-Woodward oxidation, benzophenone


ID: J42-Y2019