A Palladium-Catalyzed Borylation/Silica Gel Promoted Hydrolysis Sequence for the Synthesis of Hydroquinine-6'-Boric Acid and Its Applications.

Hydroquinine-6'-boric acid was first synthesized via a palladium-catalyzed borylation/silica gel promoted hydrolysis sequence of hydroquinine-derived triflate and bis(pinacolato)diboron. The newly designed chiral building block was subjected to the Suzuki-Miyaura cross-coupling reaction, Petasis reaction, and selenylation reaction, respectively, and all these reactions worked well to afford the corresponding 6'-functionalized hydroquinines with satisfactory results, demonstrating its extraordinary application potency.