Synthesis of thioether containing trialkoxysilanes

摘要

The invention relates to a radical-initiated thiol-ene or thiol-yne “click” reaction that provides a simple and efficient route to diverse trialkoxysilanes. Trialkoxysilanes made in this way are obtained in quantitative to near-quantitative yields with high purity without any or minimal purification. A wide range of functional groups is tolerated in this approach, and even complex alkenes click with the silane precursors. The modular nature of these radical-based thiol-ene or thiol-yne “click” reactions allows a wide variety of pendant groups to be coupled to silane compounds that can then be coupled to a wide variety surfaces in order to modify their material properties. Consequently, such radical initiated thiol-ene and thiol-yne reactions provide facile and efficient methods for preparing an enormous number of surface-active functional trialkoxysilanes.

主权项

1. A method for making a trialkoxysilane compound comprising a thioether, the method comprising the steps of:
(a) forming a mixture comprising:
a trialkoxysilane compound;a compound comprising a sulfhydryl moiety;an alkene compound or an alkyne compound; anda radical initiator agent; (b) initiating a chemical reaction in the mixture so that:
the radical initiator agent reacts with a hydrogen atom in a first sulfhydryl moiety so as to form a thiyl radical;the thiyl radical reacts with the alkene or the alkyne so as to form a radical intermediate;the radical intermediate reacts with a hydrogen atom in a second thiol moiety so as to form a thioether; so that the trialkoxysilane compound comprising the thioether is made; andthe chemical reaction in (b) produces a composition of matter wherein the trialkoxysilane compound comprising the thioether has a purity of at least 90%.