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

[Image: see text] 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 carbama...

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Autores principales: Hidasová, Denisa, Slanina, Tomáš
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10242758/
https://www.ncbi.nlm.nih.gov/pubmed/37126731
http://dx.doi.org/10.1021/acs.joc.3c00238
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author Hidasová, Denisa
Slanina, Tomáš
author_facet Hidasová, Denisa
Slanina, Tomáš
author_sort Hidasová, Denisa
collection PubMed
description [Image: see text] 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.
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spelling pubmed-102427582023-06-07 Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates Hidasová, Denisa Slanina, Tomáš J Org Chem [Image: see text] 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. American Chemical Society 2023-05-01 /pmc/articles/PMC10242758/ /pubmed/37126731 http://dx.doi.org/10.1021/acs.joc.3c00238 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Hidasová, Denisa
Slanina, Tomáš
Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates
title Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates
title_full Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates
title_fullStr Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates
title_full_unstemmed Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates
title_short Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates
title_sort triarylamminium radical cation facilitates the deprotection of tert-butyl groups in esters, ethers, carbonates, and carbamates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10242758/
https://www.ncbi.nlm.nih.gov/pubmed/37126731
http://dx.doi.org/10.1021/acs.joc.3c00238
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