Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

Overview

Journal Chemistry

Specialty Chemistry

Date 2020 Dec 3

PMID 33270278

Citations 2

Authors

Lars E Sattler

Gerhard Hilt

Affiliations

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Abstract

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

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PMID: 35230842 PMC: 8938952. DOI: 10.1021/acs.joc.2c00067.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles.

Sattler L, Hilt G Chemistry. 2020; 27(2):605-608.

PMID: 33270278 PMC: 7839530. DOI: 10.1002/chem.202004140.

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