Use of Catalytic Fluoride under Neutral Conditions for Cleaving Silicon–Oxygen Bonds

Catalytic protocols for the deprotection of silyl ethers using TBAF or CsF as fluoride sources.

You know that deprotection of silyl ethers is a common operation in organic synthesis, and that usually you use TBAF. TBAF is expensive and has other problems, so Phillips et al. (The Pennsylvania University, Penn., USA) publish here a catalytic method using TBAF as fluoride source in a THF-water reaction medium to improve things. Not only that, but they have come up also with another protocol using catalytic CsF in DMSO-MeOH. Only 5 real cases are presented, while the rest mechanistic and kinetic data, but I find it very attractive in view of the high cost of the TBAF. Let’s try…

J. Org. Chem., Article ASAP. See: 10.1021/jo200848j