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Synfacts 2025; 21(01): 76
DOI: 10.1055/a-2467-5217
Organo- and Biocatalysis

Sustainable Silane Oxidation to Silanols via Frustrated Lewis Pair Catalysis with Water

Contributor(s):
Benjamin List 
,
Wencke Leinung 
Xie F, Zhang S, Yang M, He J *, Li S *, Zhang Y *. Jilin University, Changchun and Nanjing University, P. R. China
Frustrated Lewis Pair-Promoted Organocatalytic Transformation of Hydrosilanes into Silanols with Water Oxidant.

J. Am. Chem. Soc. 2024;
146: 29373-29382
DOI: 10.1021/jacs.4c07818
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Keywords

frustrated Lewis pairs - FLP catalysis - hydrosilanes - silanols - water - oligosiloxanes

Significance

He, Li, Zhang and co-workers report a frustrated Lewis pair (FLP)-catalyzed oxidation of silanes to silanols using water as oxidant. Various silanols are selectively obtained in high to excellent yields with undesired siloxane formation being suppressed. Furthermore, a controlled synthesis of oligosiloxanes is demonstrated by an alternating FLP-promoted oxidation and Lewis acid catalyzed dehydrogenation sequence, highlighting its potential applications in designing advanced silicon-based polymer materials.


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Comment

Interestingly, mechanistic investigations reveal that water, rather than the silane, initiates the activation of the FLP, with the resulting ion pair reacting with the silane through a concerted SN2 pathway. This work presents a valuable metal-free alternative for silanol synthesis, offering advantages over photochemical, electrochemical, and enzymatic methods by employing a sustainable oxidant and reducing unwanted byproducts.


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Publication History

Article published online:
20 December 2024

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