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