A Novel, Chemoselective and Efficient Microwave-Assisted Deprotection of Silyl Ethers with Selectfluor

Abstract

A novel microwave-assisted, chemoselective and efficient method for the cleavage of silyl ethers (aliphatic and aromatic) catalyzed by Selectfluor is reported. A wide range of TBS-, TIPS-, and TBDPS-protected alkyl silyl ethers can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The chemoselective deprotection of phenolic TBS ethers, and not the TIPS- or TBDPS-protected phenolic ethers, and the deprotection of silyl esters were also achieved under these reaction conditions. In addition, the transetherification and etherification of benzylic hydroxy groups in alcoholic solvents is observed.

N-Fluorobenzenaminium tetrafluoroborate generated in situ by aniline and Selectfluor as a reusable catalyst for the ring opening of epoxides with amines under microwave irradiation

“…1,2 Its electrophilic and oxidative characteristics make it a useful catalyst for the cleavage of electron-rich protecting groups, such as p-methoxybenzylidene (PMP), tetrahydropyranyl (THP) ethers, 1,3-dithianes, the deprotection of silyl ethers and the ring opening of epoxides with ammonium thiocyanate (Scheme 1). [3][4][5] The ring opening of epoxide with an amine as a nucleophile is an important route for the synthesis of β-amino alcohols. 6 β-Amino alcohols are versatile intermediates for the synthesis of a wide range of biologically active natural and synthetic products, synthetic amino acids, β-blockers in pharmaceuticals and insecticides.…”

Cationic Copolymerization of Styrene Derivatives and Oxiranes via Concurrent Vinyl-Addition and Ring-Opening Mechanisms: Multiblock Copolymer Formation via Occasional Crossover Reactions

“… a See Figures and and Figures S17 and S18 for the spectra of the polymers. b Refs − for the monomeric compounds. …”

Recent Advances in Activation of Silicon Bonds by Fluoride Ion / Jaunākie Sasniegumi Silīcija Saišu Aktivācijās Ar Fluorīda Jonu

“…Fluoride ion-mediated desilylation of O-silyl ethers to the corresponding alcohols was widely applied in organic synthesis [106][107][108][109][110][111][112][113][114][115][116]. Some articles were dedicated to selective desilylation of O-silyl ethers.…”