Journal
ORGANIC LETTERS
Volume 25, Issue 14, Pages 2377-2381Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c00207
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We serendipitously discovered an unprecedented ring expansion reaction of 2-alkylspiroindolenines to azepinoindoles, mediated by n-tetrabutylammonium fluoride. The starting materials can be easily prepared by the oxidative dearomative spirocyclization of indole derivatives, catalyzed by hypoiodite. Mildly basic conditions and electron-deficient protecting groups for the amines were found to be crucial for promoting chemoselective reactions. Moreover, the ring expansion of aniline-derived spiroindolenines can proceed smoothly under much milder conditions using only a catalytic amount of cesium carbonate.
We serendipitously found an unprecedented 5-to-7-membered ring expansion of 2-alkylspiroindolenines to azepinoindoles mediated by n-tetrabutylammonium fluoride. The starting materials can be easily prepared by the hypoiodite-catalyzed oxidative dearomative spirocyclization of indole derivatives. Mildly basic conditions and electron-deficient protecting groups for the amines were found to be crucial to promoting chemoselective reactions. Moreover, the ring expansion of aniline-derived spiroindolenines proceeds smoothly under much milder conditions using only a catalytic amount of cesium carbonate.
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