Hydrosilylation

Hydrosilylation, also called catalytic hydrosilation, describes the addition of Si-H bonds across unsaturated bonds. Ordinarily the reaction is conducted catalytically and usually the substrates are unsaturated organic compounds. Alkenes and alkynes give alkyl and vinyl silanes; aldehydes and ketones give silyl ethers. The process was first reported in academic literature in 1947. Hydrosilylation has been called the "most important application of platinum in homogeneous catalysis."

The catalytic transformation represents an important method for preparing organosilicon compounds. An idealized transformation is the addition of triethylsilane to diphenylacetylene:

Hydrosilylation is related to hydrogenation, and similar catalysts are sometimes employed for the two catalytic processes. Popular industrial catalysts are "Speier's catalyst," H₂PtCl₆, and Karstedt’s catalyst, an alkene-stabilized platinum(0) catalyst. One prevalent mechanism, called the Chalk-Harrod mechanism, assumes an intermediate metal complex that contains a hydride, a silyl ligand (R₃Si), and the alkene substrate. The reaction usually produces anti-Markovnikov addition alkane, i.e., silicon on the terminal carbon. Variations of the Chalk-Harrod mechanism. Some cases involve insertion of alkene into M-Si bond followed by reductive elimination, the opposite of the sequence in the Chalk-Harrod mechanism. In certain cases, hydrosilylation results in vinyl or allylic silanes resulting from beta-hydride elimination.

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