Computed thermodynamic stabilities of silylium Lewis base adducts

Abstract

We report a computational study of the transfer of silylium from phosphine to heteroatom containing Lewis bases including ethers, phosphines, and amines. The relative free energies of these compounds are compared to develop a thermodynamic scale of stabilities that can help to interpret the chemoselectivity observed with complex natural products and biomass-derived sugars. Both the choice of silane and the phosphine Lewis base impact the thermodynamics of this transfer.