KHF₂, a mild and selective desilylating agent for phenol t-butyldimethylsilyl (TBDMS) ethers.

ABSTRACT: TBDMS (t-BuMe₂Si, t-butyldimethylsilyl) ethers of a variety of phenols have been deprotected with KHF₂ in MeOH, at room temperature. Carboxylic ester and labile phenolic acetate were unaffected under these conditions. In competition reactions between TBDMS ethers of a phenol and two primary benzylic alcohols, the phenolic ether underwent cleavage whereas the alcohol ethers remained intact. From a substrate containing both a phenolic hydroxyl group and a secondary, doubly benzylic hydroxyl group protected as TBDMS ethers, the phenol was rapidly and selectively released. Cleavage of TBDMS, TBDPS, and TIPS ethers of a phenol was also compared. TBDMS and TBDPS ethers underwent cleavage at room temperature within 30 min, whereas removal of the TIPS ether requ

SUBMITTER: Lakshman MK 

PROVIDER: S-EPMC5509224 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature