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Late stage C–H functionalization via chalcogen and pnictogen salts
Late-stage functionalization (LSF) of heteroarenes can dramatically accelerate SAR studies by enabling the installation of functional groups that would otherwise complicate a synthetic sequence. Although heteroaryl halides and boronic esters have well-established chemistries for LSF, alternatives th...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162414/ https://www.ncbi.nlm.nih.gov/pubmed/34094266 http://dx.doi.org/10.1039/d0sc03833d |
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author | Kelly, Christopher B. Padilla-Salinas, Rosaura |
author_facet | Kelly, Christopher B. Padilla-Salinas, Rosaura |
author_sort | Kelly, Christopher B. |
collection | PubMed |
description | Late-stage functionalization (LSF) of heteroarenes can dramatically accelerate SAR studies by enabling the installation of functional groups that would otherwise complicate a synthetic sequence. Although heteroaryl halides and boronic esters have well-established chemistries for LSF, alternatives that enable site-selective C–H functionalization are highly attractive. Recently, three unrelated cationic groups (phosphonium, pyridinium, and thianthrenium), which can replace C–H bonds late stage, have been identified as precursors to various functional groups. This review will discuss the synthesis and application of these three salts with an emphasis on their use for LSF and application to medicinal chemistry. |
format | Online Article Text |
id | pubmed-8162414 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81624142021-06-04 Late stage C–H functionalization via chalcogen and pnictogen salts Kelly, Christopher B. Padilla-Salinas, Rosaura Chem Sci Chemistry Late-stage functionalization (LSF) of heteroarenes can dramatically accelerate SAR studies by enabling the installation of functional groups that would otherwise complicate a synthetic sequence. Although heteroaryl halides and boronic esters have well-established chemistries for LSF, alternatives that enable site-selective C–H functionalization are highly attractive. Recently, three unrelated cationic groups (phosphonium, pyridinium, and thianthrenium), which can replace C–H bonds late stage, have been identified as precursors to various functional groups. This review will discuss the synthesis and application of these three salts with an emphasis on their use for LSF and application to medicinal chemistry. The Royal Society of Chemistry 2020-09-07 /pmc/articles/PMC8162414/ /pubmed/34094266 http://dx.doi.org/10.1039/d0sc03833d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Kelly, Christopher B. Padilla-Salinas, Rosaura Late stage C–H functionalization via chalcogen and pnictogen salts |
title | Late stage C–H functionalization via chalcogen and pnictogen salts |
title_full | Late stage C–H functionalization via chalcogen and pnictogen salts |
title_fullStr | Late stage C–H functionalization via chalcogen and pnictogen salts |
title_full_unstemmed | Late stage C–H functionalization via chalcogen and pnictogen salts |
title_short | Late stage C–H functionalization via chalcogen and pnictogen salts |
title_sort | late stage c–h functionalization via chalcogen and pnictogen salts |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162414/ https://www.ncbi.nlm.nih.gov/pubmed/34094266 http://dx.doi.org/10.1039/d0sc03833d |
work_keys_str_mv | AT kellychristopherb latestagechfunctionalizationviachalcogenandpnictogensalts AT padillasalinasrosaura latestagechfunctionalizationviachalcogenandpnictogensalts |