Synthesis of a Base-Stabilized 1-Hydrosilanimine

In this experiment, the synthesis of the first donor-stabilized hydrosilanimine by the reaction of RSiHCl2 (R = Ar(SiMe3)N, Ar = 2,6-tPr2C6H3) with N-heterocyclic carbenes 1,3,4,5-tetramethylimidazol-2-ylidene (IMe4) was described. 

Schlenk flask, magnetic stirrer, vacuum pump, low-temperature bath, constant pressure funnel, safety glasses, laboratory coat, and protective gloves. 

The product is highly reactive and air-sensitive. All experiments were carried out under an atmosphere of dry argon or nitrogen by using modified Schlenk line and glovebox techniques. THF, 

A solution of ArN SiMe3)SlHCl2 (0.35 g, 1.00 mmol) in THF (5 mL) was added to a solution of IMe4 (0.25 g, 2 mmol) in THF (5 mL) at — 78°C. The mixture was allowed to warm up to room temperature and stirred overnight. All volatile compounds were removed, and the remaining residual was extracted with n-hexane. Removal of solvents and crystallization from toluene at —30°C yielded yellow crystals (yield 0.15 g, 26%). 

The donor-stahilized hydrosilanimine is potentially useful as a hydrosilylation reagent. In addition, the existence of the Si=N double bond allows the cycloaddition reactions with unsaturated organic molecules for the synthesis of silicon heterocycles. 

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