Carbon Bond Formation with Cyanosilanes

Carbon-Carbon Bond Formation with Cyanosilanes 

Cyanotrimethylsilane (TMSCN) is one of fhe most versatile sihcon reagents in or- 

Although HCN also adds to these unsaturated bonds to afford cyanohydrins and a-amino nitriles, use of TMSCN instead of HCN provides an efficient and safer route to these compounds. Cyanosilylation with TMSCN is accelerated by acid and base catalysts. In recent years a variety of organic and inorganic compounds have been found to work as effective catalysts, and much attention has been devoted for the development of chiral catalysts for asymmetric cyanosilylation of aldehydes, ketones, and imines. 

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Carbon-Carbon Bond Formation with Cyanosilanes... 

Cyanosilanes can be isocyanide sources since a tautomeric equilibrium exists between cyanosilanes and the corresponding isocyanides. The equilibrium largely favors the cyano tautomer. The use of such dilute isocyanide donors realizes efficient Ti(n)- and Ni(0)-catalyzed cyclizations of enynes to iminocyclopentenes via metallacyclopentene intermediates (Scheme 19).266,266 266b Treatment of zirconacyclopentanes and -pentenes with Me3SiCN provides zirconocene-imine complexes, which serve for carbon-carbon bond formation with various unsaturated bonds.267... 

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