Electrophilic aromatic substitution of a BN indole |
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Authors: | Abbey Eric R Zakharov Lev N Liu Shih-Yuan |
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Institution: | Department of Chemistry, University of Oregon, Eugene, Oregon 97403, United States. |
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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. |
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