Electrophilic Aromatic Substitution of a BN Indole

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2010 Nov 4

PMID 21043508

Citations 16

Authors

Eric R Abbey

Lev N Zakharov

Shih-Yuan Liu

Affiliations

Soon will be listed here.

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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