Chemoselective Chemical and Electrochemical Deprotections of Toluates

Significance

A chemoselective deprotection of toluic acid esters by using either SmI₂/HMPT or by electrolysis in the presence of a proton source is reported. In short reaction times a variety of functionalized alcohols can be obtained from the respective toluates in overall high yields, the chemical deprotection generally affording slightly improved yields over the electrochemical reduction. The presence of pivalic or acetic esters is tolerated, thus enabling in the case of polyols the selective saponification of just the toluate-protected hydroxyl group.