Neutral-Eosin-Y-Photocatalyzed Silane Chlorination Using Dichloromethane

Angew Chem Int Ed Engl. 2019 Sep 2;58(36):12580-12584. doi: 10.1002/anie.201908556. Epub 2019 Aug 5.

Abstract

Chlorosilanes are versatile reagents in organic synthesis and material science. A mild pathway is now reported for the quantitative conversion of hydrosilanes to silyl chlorides under visible-light irradiation using neutral eosin Y as a hydrogen-atom-transfer photocatalyst and dichloromethane as a chlorinating agent. Stepwise chlorination of di- and trihydrosilanes was achieved in a highly selective fashion assisted by continuous-flow micro-tubing reactors. The ability to access silyl radicals using photocatalytic Si-H activation promoted by eosin Y offers new perspectives for the synthesis of valuable silicon reagents in a convenient and green manner.

Keywords: Si−H activation; dichloromethane; hydrogen atom transfer; neutral eosin Y; silyl chloride.