Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates.

ABSTRACT

We report a catalytic protocol for mild OtBu deprotection using two commercial reagents the tris-4-bromophenylamminium radical cation, commonly known as magic blue (MB•+), and triethylsilane. Magic blue catalytically facilitates the cleavage of the C-O bond in tert-butyl carbamates, carbonates, esters, and ethers in a high isolated yield of up to 95%, and sacrificial triethylsilane accelerates the reaction. Without requiring high temperatures, transition metals, or strong acidic or basic catalysts, this method is suitable for structurally diverse compounds, including aliphatic, aromatic, and heterocyclic substrates.