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Transfer Hydrosilylation.

Martin Oestreich¹

¹Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de. martin.oestreich@tu-berlin.de.

Angewandte Chemie (International Ed. in English)

|November 25, 2015

Summary

Recent advances introduce radical and ionic transfer hydrosilylation methods. These novel techniques utilize silicon-substituted cyclohexa-1,4-diene for efficient hydrosilylation, showing promising industrial and academic potential.

Keywords:

cations cyclohexa-1,4-dienes hydrosilylation radicals silane transfer

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Transfer hydrogenation is a widely used industrial and academic technology.
Transfer hydrosilylation methods were largely unreported prior to recent advancements.
Existing methods lacked efficient and versatile approaches for silicon-based transformations.

Purpose of the Study:

To introduce and contextualize novel radical and ionic transfer hydrosilylation methods.
To explore the mechanistic basis of these new hydrosilylation techniques.
To highlight the potential of transfer hydrosilylation in synthetic chemistry.

Main Methods:

Development of a radical transfer hydrosilylation pathway.
Development of an ionic transfer hydrosilylation pathway.
Utilizing silicon-substituted cyclohexa-1,4-diene as a key precursor in both methods.

Main Results:

Successful demonstration of both radical and ionic transfer hydrosilylation.
Mechanisms involve aromatization of cyclohexadienyl radical/cation intermediates.
Concomitant homo- or heterolytic fission of the Si-C bond drives the reactions.

Conclusions:

Recent advancements have established viable radical and ionic transfer hydrosilylation methods.
These methods offer a promising new avenue for silicon-based organic synthesis.
Despite current limitations, transfer hydrosilylation holds significant potential for future applications.