Cargando…
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...
Autores principales: | , |
---|---|
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 |
_version_ | 1785054287094611968 |
---|---|
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. |
format | Online Article Text |
id | pubmed-10242758 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT hidasovadenisa triarylamminiumradicalcationfacilitatesthedeprotectionoftertbutylgroupsinestersetherscarbonatesandcarbamates AT slaninatomas triarylamminiumradicalcationfacilitatesthedeprotectionoftertbutylgroupsinestersetherscarbonatesandcarbamates |