Frustrated Lewis Pair-Promoted Organocatalytic Transformation of Hydrosilanes into Silanols with Water Oxidant

Owing to their unique properties, the silanols have attracted intense attention but remain challenging to prepare from the organocatalytic oxidation of hydrosilanes using H<sub>2</sub>O as a green oxidant. Herein, we employ a frustrated Lewis pair (FLP) to successfully suppress the formation of undesired siloxanes and produce silanols in high to excellent yields in the presence of H<sub>2</sub>O. Mechanistic studies suggest that the reaction is initiated with the activation of FLP by H<sub>2</sub>O rather than by silanes and goes through a concerted S<sub>N</sub>2 mechanism. More importantly, the combination of the FLP-catalyzed oxidation of hydrosilanes with B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalyzed dehydrogenation enables us to realize the precise synthesis of sequence-controlled oligosiloxanes. This method exhibits a broad substrate scope and can be easily scaled up, thus exhibiting promising application potentials in the precision synthesis of silicon-containing polymer materials.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2024-10-16
DOI
https://doi.org/10.1021/jacs.4c07818
Citations
9
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
2.25

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article

Frustrated Lewis Pair-Promoted Organocatalytic Transformation of Hydrosilanes into Silanols with Water Oxidant

Mo Yang, Sutao Zhang, Yuetao Zhang, Jianghua He et al.
9 citations
Journal of the American Chemical Society
Organoboron and organosilicon chemistry
2.25
article

Frustrated Lewis Pair-Promoted Organocatalytic Transformation of Hydrosilanes into Silanols with Water Oxidant

Mo Yang, Sutao Zhang, Yuetao Zhang, Jianghua He, Shuhua Li, Fuyu Xie
article en
9 citations

Abstract

Owing to their unique properties, the silanols have attracted intense attention but remain challenging to prepare from the organocatalytic oxidation of hydrosilanes using H<sub>2</sub>O as a green oxidant. Herein, we employ a frustrated Lewis pair (FLP) to successfully suppress the formation of undesired siloxanes and produce silanols in high to excellent yields in the presence of H<sub>2</sub>O. Mechanistic studies suggest that the reaction is initiated with the activation of FLP by H<sub>2</sub>O rather than by silanes and goes through a concerted S<sub>N</sub>2 mechanism. More importantly, the combination of the FLP-catalyzed oxidation of hydrosilanes with B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalyzed dehydrogenation enables us to realize the precise synthesis of sequence-controlled oligosiloxanes. This method exhibits a broad substrate scope and can be easily scaled up, thus exhibiting promising application potentials in the precision synthesis of silicon-containing polymer materials.

Journal of the American Chemical SocietyVol. 146(43)
Jilin University (CN), Jilin Medical University (CN), Ministry of Education and Child Care (CA), State Key Laboratory of Supramolecular Structure and Materials, Nanjing University (CN)
National Natural Science Foundation of China
Clean water and sanitation
Openalex Percentile: Top 12%
Organoboron and organosilicon chemistry
2.25
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Frustrated Lewis Pair-Promoted Organocatalytic Transformation of Hydrosilanes into Silanols with Water Oxidant — Mo Yang, Sutao Zhang, et al. · Journal of the American Chemical Society (2024) | TGRS Research Map | TGRS