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Electrophilic aromatic substitution of a BN indole.

ABSTRACT: We report the first examples of a "BN-fused" indole, and we demonstrate that this new family of unnatural indole derivatives undergoes electrophilic aromatic substitution (EAS) reactions with the same regioselectivity as its organic analogue. Competition experiments reveal that N-t-Bu-BN-indole is more nucleophilic in EAS reactions than its carbonaceous counterpart. X-ray structural analysis between BN indole and classic indole highlights significant differences in bond distances, in particular for bonds associated with the boron atom.

SUBMITTER: Abbey ER

PROVIDER: S-EPMC2990470 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Electrophilic aromatic substitution of a BN indole.

Abbey Eric R ER Zakharov Lev N LN Liu Shih-Yuan SY

Journal of the American Chemical Society 20101102 46

We report the first examples of a "BN-fused" indole, and we demonstrate that this new family of unnatural indole derivatives undergoes electrophilic aromatic substitution (EAS) reactions with the same regioselectivity as its organic analogue. Competition experiments reveal that N-t-Bu-BN-indole is more nucleophilic in EAS reactions than its carbonaceous counterpart. X-ray structural analysis between BN indole and classic indole highlights significant differences in bond distances, in particular ...[more]

PMID: 21043508

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