Synthesis of anti-vicinal diboronates from diarylethynes and B₂pin₂

Anti-vicinal diboronates were fabricated from easily available diarylethynes and B₂pin₂ via a base-catalyzed domino-borylation-protodeboronation (DBP) strategy under transition-metal-free conditions. Under the standard conditions, reactants with a range of different classes of functional groups on the rings, such as MeO, MeS, CF₃O, Me₂N, TMS, I, Br, Cl, F, and the thiophene ring, were tolerated. Downstream transformation of the vicinal diboronates provided a facile pathway for obtaining vicinal diols by mild oxidation with NaBO₃, and a new deuteriation technique was developed in order to acquire 1,2-diarylethanes-1,2-d₂ and 1,2-diarylethanes-1,1,2,2-d₄. The new deuteriation strategy developed in this study may provide a new research direction for deuteriation chemistry.