Easy access to nucleophilic boron through diborane to magnesium boryl metathesis

摘要: Organoboranes are some of the most synthetically valuable and widely used intermediates in organic pharmaceutical chemistry. Their synthesis, however, is limited by behaviour common boron starting materials as archetypal Lewis acids such that routes to organoboranes rely on reactivity an electrophile. While realization convenient sources nucleophilic boryl anions would open up a wealth opportunity for development new organoboranes, synthesis current candidates generally need highly reducing reaction conditions. Here, we report simple magnesium through heterolytic activation B-B bond bis(pinacolato)diboron, which achieved treatment easily generated diboranate complex with 4-dimethylaminopyridine. The shown act unambiguous nucleophile its reactions iodomethane, benzophenone N,N'-di-isopropyl carbodiimide density functional theory.