(Indol-3-yl)(DMIX)Iodonium Salts: Novel Electrophilic Indole Reagents

A new umpolung approach to the C3–H functionalization of indoles with diverse nucleophiles based on the intermediate formation of I­(III) reagents is described. The 3,5-dimethylisoxazol-4-yl auxiliary allows for selective indole transfer under catalyst-free conditions, which was impossible using pre...

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Bibliographic Details
Published in:Organic letters 2024-04, Vol.26 (15), p.3189-3194
Main Authors: Bugaenko, Dmitry I., Malashchenko, Nikolai A., Kopytov, Sergei O., Lukonina, Natalia S., Karchava, Alexander V.
Format: Article
Language:English
Subjects:
indoles
iodine
Lewis acids
Lewis bases
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Summary:A new umpolung approach to the C3–H functionalization of indoles with diverse nucleophiles based on the intermediate formation of I­(III) reagents is described. The 3,5-dimethylisoxazol-4-yl auxiliary allows for selective indole transfer under catalyst-free conditions, which was impossible using previously reported reagents. Combining the mildness of transition-metal-free conditions and the high reactivity of hypervalent iodine reagents, this protocol tolerates various functional groups and provides access to indoles that are difficult to prepare conventionally.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c00797