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

0571445 - ÚOCHB 2024 RIV US eng J - Článek v odborném periodiku
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
Grant CEP: GA ČR(CZ) GJ19-20467Y
Institucionální podpora: RVO:61388963
Klíčová slova: C-H oxidation * protecting group * cleavage
Obor OECD: Organic chemistry
Impakt faktor: 3.6, rok: 2022
Způsob publikování: 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.
Trvalý link: https://hdl.handle.net/11104/0342663