Synthesis of anti-vicinal diboronates from diarylethynes and Bpin.

Anti-vicinal diboronates were fabricated from easily available diarylethynes and Bpin 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, CFO, MeN, 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 NaBO, and a new deuteriation technique was developed in order to acquire 1,2-diarylethanes-1,2-d and 1,2-diarylethanes-1,1,2,2-d. The new deuteriation strategy developed in this study may provide a new research direction for deuteriation chemistry.