Catechol‐Mediated Redox‐Neutral One‐pot Transformation of SiO2into SiPh4

Abstract

AbstractOrganosilanes range among the most important products in chemical industries. Unfortunately, their bulk production starting from silicon oxides has a substantial ecological footprint due to the immense energy consumption and the numerous hazardous by‐products imposed by the redox cycling between Si(0) and Si(IV). Herein, we report the first redox‐neutral, one‐pot silicon−carbon bond formation starting from silica gel by combining catechol‐mediated SiO2depolymerization and nucleophilic substitution of the tris(catecholato)silicate dianion intermediates. Screening and optimization of the individual steps enables a 76 % yield of SiPh4on a preparative scale. Non‐rationalizable effects of solvents, nucleophiles, and countercations are identified, rendering suitable for statistical optimization approaches such as “design‐of‐experiments” in future studies. The general success of such process encourages the search for more energy‐ and waste‐effective organosilane production.