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

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Abstract

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.

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

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Publication details

The article was received on 08 May 2017, accepted on 05 Jul 2017 and first published on 12 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB01127J
Citation: Org. Biomol. Chem., 2017, Advance Article
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    The synthesis of polysubstituted indoles from 3-bromo-2-indolyl phosphates

    P. Polák and T. Tobrman, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01127J

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