シラノール新規合成法の開発

抄録

Organosilanols are now attracting more and more attentions due to its usefulness for metal-catalyzed cross-coupling reactions. Among the most powerful methods are Stille, Suzuki, and Negishi couplings, but they have some problems such as toxicity (Sn) or handling (B, Zn). On the other hand, organosilanols are more environmentally friendly, less hazardous and easier to handle, which can provide a viable alternative to those problems. Therefore effectively preparing silanol compounds has profound meanings.
During our study, we found a new method for preparing silanols: oxidation of silylmethanols to silanols. After we optimized its reaction conditions, TEMPO oxidation turned out to be the most successful method. This reaction was extended to several kinds of silylmethanols and most of them gave corresponding silanols in good to excellent yields. Furthermore, we also found that bromomethylsilanes were converted into silanols when reacted with TMANO.