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The synthesis of polysubstituted indoles from 3-bromo-2-indolyl phosphates

A novel methodology for the synthesis of functionalised indoles based on the cross-coupling reactions of 3-bromo-2-indolyl phosphates is described. The preparation involves the conversion of easily available 2-oxindoles to 3,3-dibromo-2-oxindoles followed by the Perkow reaction affording 3-bromo-2-i...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017-07, Vol.15 (29), p.6233-6241
Main Authors: Polák, Peter, Tobrman, Tomáš
Format: Article
Language:English
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Summary:A novel methodology for the synthesis of functionalised indoles based on the cross-coupling reactions of 3-bromo-2-indolyl phosphates is described. The preparation involves the conversion of easily available 2-oxindoles to 3,3-dibromo-2-oxindoles followed by the Perkow reaction affording 3-bromo-2-indolyl phosphates. Then bromine atom is substituted regioselectively by the Suzuki coupling reaction. We observed that aluminum chloride promoted the reaction of 3-substituted-2-indolyl phosphates with organozinc reagents furnishing 2,3-disubstituted indoles as final products. The overall diversity and efficiency of the methodology was demonstrated by the synthesis of bioactive molecule from easily available substances.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01127j