The Propargyl Rearrangement to Functionalised Allyl-Boron and Borocation Compounds

A diverse range of Lewis acidic alkyl, vinyl and aryl boranes and borenium compounds that are capable of new carbon-carbon bond formation through selective migratory group transfer have been synthesised. Utilising a series of heteroleptic boranes [PhB(C6F5)(2) (1), PhCH2CH2B(C6F5)(2) (2), and E-B(C6F5)(2)(C6F5)C=C(I)R (R=Ph 3a, nBu 3b)] and borenium cations [phenylquinolatoborenium cation ([QOBPh][AlCl4], 4)], it has been shown that these boron-based compounds are capable of producing novel allyl- boron and boronium compounds through complex rearrangement reactions with various propargyl esters and carbamates. These reactions yield highly functionalised, synthetically useful boron substituted organic compounds with substantial molecular complexity in a one-pot reaction.