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

0571445 - ÚOCHB 2024 RIV US eng J - Journal Article
Hidasová, Denisa - Slanina, Tomáš
Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates.
Journal of Organic Chemistry. Roč. 88, č. 11 (2023), s. 6932-6938. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA ČR(CZ) GJ19-20467Y
Institutional support: RVO:61388963
Keywords : C-H oxidation * protecting group * cleavage
OECD category: Organic chemistry
Impact factor: 3.6, year: 2022
Method of publishing: Open access
https://doi.org/10.1021/acs.joc.3c00238

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.
Permanent Link: https://hdl.handle.net/11104/0342663