Silanol Salt for Deprotection Reactions and Cross-coupling Reactions

Potassium trimethylsiloxide (1) is used not only in the dealkylation of esters^1,2) but also as a base in Suzuki-Miyaura cross-coupling,³⁾ in the disconnection of carbon-silicon bond⁴⁾ and hydrolysis of nitriles.⁵⁾ It is considered that the dealkylation of esters using 1 mainly proceeds through a nucleophilic attack of the silanolate anion and can be performed under milder conditions when compared to other reagents with the same reaction mechanism. In Suzuki-Miyaura cross-coupling, the reaction can proceed rapidly under anhydrous conditions. Moreover, the protodesilylation reaction requires only catalytic amount of 1 and the sp³, sp² and sp carbon-silicon bonds are easily disconnected. In this way, a number of reports are increasing recently due to the wide variety of application of 1.