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Metal-free selective mono-halodecarboxylation of heteroarenes under mild conditions.

ABSTRACT: The halodecarboxylation of heteroarene carboxylic acids by treatment with N-bromosuccinimide or N-chlorosuccinimide was performed. This procedure provides a convenient route to synthetically useful mono-halogenated heteroarene intermediates such as halo-indoles, -aza-indoles, -indazoles and -aza-indazoles. The mild conditions employed and simple protocol provides an advantage over traditional halodecarboxylation procedures that require expensive and toxic metal catalysts, basic conditions, time-consuming intermediate isolation and elevated reaction temperatures.

SUBMITTER: Henderson SH

PROVIDER: S-EPMC6030312 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Metal-free selective mono-halodecarboxylation of heteroarenes under mild conditions.

Henderson Scott H SH West Ryan A RA Ward Simon E SE Honey Mark A MA

Royal Society open science 20180620 6

The halodecarboxylation of heteroarene carboxylic acids by treatment with <i>N</i>-bromosuccinimide or <i>N</i>-chlorosuccinimide was performed. This procedure provides a convenient route to synthetically useful mono-halogenated heteroarene intermediates such as halo-indoles, -aza-indoles, -indazoles and -aza-indazoles. The mild conditions employed and simple protocol provides an advantage over traditional halodecarboxylation procedures that require expensive and toxic metal catalysts, basic con ...[more]

PMID: 30110478

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