Borane-Catalyzed Ring-Opening and Ring-Closing Cascades of Furans Leading to Silicon-Functionalized Synthetic Intermediates
Sehoon Park and Sukbok Chang report a borane-catalyzed synthesis of silicon-functionalized synthetic intermediates.
A number of transition-metal complexes are known to efficiently catalyze hydrosilylation of unsaturated functionalities including C=O, C=N and C=C bonds, largely via inner- or outer-sphere pathways. Most of the presently available hydrosilylation processes rely on the use of expensive transition metals (Rh, Ir, Pt, or Pd). In this regard, certain Lewis acids such as B(C6F5)3 have drawn significant attention as catalysts due to their practical merits. Over the past 20 years, the B(C6F5)3 catalyst system has been shown to be effective not only for hydrosilylation of unsaturated functionalities but also for reductive sp3-C–X bond cleavage (X = O, S, or halides) using hydrosilanes. The Park and Chang group from the Institute for Basic Science and KAIST (Daejeon, South Korea) recently reported the B(C6F5)3-catalyzed dearomative silylative reduction of quinolines and pyridines leading to (partially) saturated azacyclic products having sp3-C–Si bonds beta to the nitrogen atom.
Read the full article here: Borane-Catalyzed Ring-Opening and Ring-Closing Cascades of Furans Leading to Silicon-Functionalized Synthetic Intermediates