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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...

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Detalles Bibliográficos
Autores principales: Kelly, Christopher B., Padilla-Salinas, Rosaura
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
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.
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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
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