Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 21, Issue 36, Pages 7290-7294Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3ob00985h
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We report a protonic-acid-promoted electrosynthetic strategy for the dearomative dibromocyclization of tryptamine/tryptophol derivatives for the convenient late-stage 3,5-diversification of heterocyclic indolines.
Electrophilic bromocyclization reactions are widely used as key steps in the synthesis of diverse functionalized tetrahydrofuroindolines and hexahydropyrroloindolines. However, the direct dibromination variants of these reactions for the synthesis of 3,5-dibromoindolines remain undeveloped. Here, we report a protonic-acid-promoted electrooxidative protocol for the dearomative C3,C5-dibromocyclizations of tryptophol and tryptamine derivatives. This electrosynthetic approach, which enables direct selective construction of heterocyclic 3a,5a-dibromoindolines with inexpensive, non-hazardous NaBr as both the electrolyte and Br source, provides a convenient, practical method for the late-stage 3,5-diversification of heterocyclic indolines. We report a protonic-acid-promoted electrosynthetic strategy for the dearomative dibromocyclization of tryptamine/tryptophol derivatives for the convenient late-stage 3,5-diversification of heterocyclic indolines.
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