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Hydrosilane Useful for Hydrogenation and Hydroalkylation of Alkenes

Isopropoxy(phenyl)silane (1) is a compound in which one of the hydrogen atoms of phenylsilane (2) is replaced by an isopropoxy group, and 1 is also known as RubenSilane.1) In the presence of a manganese catalyst, 1 can be used as a reducing agent in the hydrogenation of alkenes. Compared with 2, the use of 1 allows improvements in various reaction conditions, such as reduced catalyst loading, lower reaction temperature, and a broader range of applicable solvents and substrates.1)
Furthermore, 1 can also be used in the iron-catalyzed hydroalkylation of alkenes using benzyl bromide derivatives or redox-active alkylcarboxylic acid N-hydroxyphthalimide esters as alkyl sources.2,3) In this reaction, the alkyl group adds to the more substituted carbon atom, exhibiting Markovnikov-type selectivity. Using trisubstituted alkenes enables the formation of quaternary carbon centers, making this method promising for synthesizing complex natural products and target molecules that are difficult to access by conventional approaches.

Hydrosilane Useful for Hydrogenation and Hydroalkylation of Alkenes

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References

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