Visible-Light-Induced Aerobic Oxidation of Tertiary Silanes to Silanols using Molecular Oxygen as an Oxidant

Abstract

The photocatalyzed synthesis of silanols from tertiary silanes has been carried out using eosin Y under air. This is a metal-free method which uses a low catalyst loading, atmospheric oxygen as the oxidant, and visible light conditions (blue light).

Catalytic Synthesis of Silanols by Hydroxylation of Hydrosilanes: From Chemoselectivity to Enantioselectivity

“…First, the activation of rose bengal, then interacts with Most recently, Gui and coworkers found the oxidation of hydrosilanes to silanols could be achieved by using eosin Y as the photocatalysis. [87] The reaction was performed using O 2 as the oxidant under blue light irradiation. an array of monohydrosilanes converted into the desired silanols in high yields (27 examples, 71-99 % yields) (Scheme 47).…”

“…Most recently, Gui and coworkers found the oxidation of hydrosilanes to silanols could be achieved by using eosin Y as the photocatalysis [87] . The reaction was performed using O 2 as the oxidant under blue light irradiation.…”

Utilization of Silanols in Transition Metal-Catalyzed Organic Synthesis

“…The employed catalysts are organocatalyst or Cs base, manganese catalyst, and iron catalyst . Recent atypical approaches for silanol synthesis include the electrochemical transformation, while photocatalytic reactions are also widely employed . As a new trend, Arnold recently reported an enzymatic oxidation of hydrosilanes using evolved enzyme …”

Visible Light-Mediated Organoboron-Catalyzed Metal-Free Synthesis of Silanols from Silanes

“…With the development of photoredox catalysis in the last decade, the photo-induced oxidation of silane has also progressed significantly ( Scheme 1 c) [ 34 , 35 , 36 , 37 ]. In 2021, Chen, Fan, and their colleagues reported that under the irradiation of white light, Ru(bpy) 3 Cl 2 could catalyze the formal dehydrogenative reactions between silanes and water to produce silanols [ 38 ].…”

“…In 2018, Wang reported that the conversion of silanes to silanols could be accomplished using Rose Bengal as a photocatalyst, oxygen as an oxidant, and water as an additive [ 37 ]. Subsequently, He and Zhang reported the conversion of silane to silanol using eosin Y as a photocatalyst [ 34 ]. The study of photoinduced synthesis of silanol inspired us to consider whether the photocatalyst aminoquinolate B,B-diphenyl complex AQDAB [ 39 , 40 ], which was developed by our group and applied in photooxidation reactions [ 40 , 41 , 42 ], could induce such transformations.…”