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

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Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-05-01 , DOI: 10.1021/acs.joc.3c00238
Denisa Hidasová ₁ , Tomáš Slanina ₁

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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.

中文翻译：

三芳基铵自由基阳离子促进酯、醚、碳酸酯和氨基甲酸酯中叔丁基的脱保护

我们报告了使用两种商业试剂进行温和Ot Bu脱保护的催化方案：三-4-溴苯铵自由基阳离子，通常称为魔幻蓝 (MB ^•+ ) 和三乙基硅烷。魔幻蓝催化促进氨基甲酸叔丁酯、碳酸酯、酯和醚中 C-O 键的裂解，分离产率高达 95%，牺牲三乙基硅烷加速反应。无需高温、过渡金属或强酸或强碱催化剂，该方法适用于结构多样的化合物，包括脂肪族、芳香族和杂环底物。

更新日期：2023-05-01

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