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Iodonium Cation‐Pool Electrolysis for the Three‐Component Synthesis of 1,3‐Oxazoles
Author(s) -
Sattler Lars E.,
Hilt Gerhard
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004140
Subject(s) - acetonitrile , chemistry , electrolysis , regioselectivity , alkyne , iodine , ring (chemistry) , solvent , ion , medicinal chemistry , organic chemistry , electrolyte , electrode , catalysis
The synthesis of 1,3‐oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation‐pool electrolysis of I 2 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.