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

ABSTRACT: The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I₂ 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.

SUBMITTER: Sattler LE

PROVIDER: S-EPMC7839530 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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

Sattler Lars E LE Hilt Gerhard G

Chemistry (Weinheim an der Bergstrasse, Germany) 20201203 2

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I<sub>2</sub> in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I<sup>+</sup> 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 nak ...[more]

PMID: 33270278

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