Electrophilic aromatic substitution of a BN indole.
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.
Department of Chemistry, University of Oregon, Eugene, Oregon 97403, United States.
Eric R
ER
Abbey
Lev N
LN
Zakharov
Shih-Yuan
SY
Liu
D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D007211:Indoles; C030374:indole