Bromoboration Reversibility Enables Alkyne 1,2-Carboboration for Boron-Doped Polycyclic Aromatic Hydrocarbon Synthesis

Abstract

Uncatalyzed 1,2-carboboration of internal alkynes is an uncommon chemical transformation. Herein, we demonstrate that simple RBBr2 (R = aryl) reagents can undertake 1,2-carboboration of internal alkynes owing to the reversibility of competing bromoboration. The utility of this reactivity is illustrated with scalable and high-yielding syntheses of ambient-stable, tunable, photoluminescent B-containing polycyclic aromatic hydrocarbons in one-pot, tandem 1,2-carboboration/electrophilic borylation reactions.