Reduction of carbonyl compounds promoted by silicon hydrides under the influence of trimethylsilyl-based reagents

Abstract

The synthetic utility of hydrosilanes under the influence of trimethylsilyl-based reagents as new reducing systems is described. 1,1,3,3-Tetramethyldisiloxane (TMDS) reagent in combination with iodotrimethylsilane or bromotrimethylsilane produces alkyl halides from aldehydes in good to excellent yields. Polymethylhydrosiloxane (PMS) in the presence of iodotrimethylsilane also produces benzyl iodides in excellent yields. On the contrary, PMS reagent was found unsuitable for the synthesis of benzyl bromides. Similarly, TMDS reagent in combination with trimethylsilyl triflate produces symmetrical ethers from aldehydes without concomitant formation of competitive products. Under similar conditions, PMS reagent failed to provide the expected symmetrical ethers and Friedel–Crafts products were formed. Reduction of quinones to hydroquinones is also described.