Boron in Disguise: The Parent “Fused” BN Indole

“Fused” BN indoles are an emerging class of boron-containing indole mimics, featuring geometric structure and electophilic aromatic substitution reactivity similar to those of indoles but exhibiting distinct electronic structure, leading to unique optoelectronic properties. Herein we report the synthesis of the parent N-H BN indole and provide a head-to-head comparison of the structural features, pKa values, and optoelectronic properties of this hybrid organic/inorganic indole with the classic natural indole.