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Aromatic C-H amination in hexafluoroisopropanol.

ABSTRACT: We report a direct radical aromatic amination reaction that provides unprotected anilines with an improvement in the substrate scope compared to prior art. Hydrogen bonding by the solvent hexafluoroisopropanol to anions of cationic species is responsible for increased reactivity and can rationalize the enhancement in substrate scope. Our findings may have bearings on radical additions to arenes for direct C-H functionalization in general.

SUBMITTER: D'Amato EM

PROVIDER: S-EPMC6385662 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Aromatic C-H amination in hexafluoroisopropanol.

D'Amato Erica M EM Börgel Jonas J Ritter Tobias T

Chemical science 20190111 8

We report a direct radical aromatic amination reaction that provides unprotected anilines with an improvement in the substrate scope compared to prior art. Hydrogen bonding by the solvent hexafluoroisopropanol to anions of cationic species is responsible for increased reactivity and can rationalize the enhancement in substrate scope. Our findings may have bearings on radical additions to arenes for direct C-H functionalization in general. ...[more]

PMID: 30881670

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