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Iodonium Cation‐Pool Electrolysis for the Three‐Component Synthesis of 1,3‐Oxazoles
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AbstractThe 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.
Title: Iodonium Cation‐Pool Electrolysis for the Three‐Component Synthesis of 1,3‐Oxazoles
Description:
AbstractThe 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.
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