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A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent

Methylation is one of the most fundamental conversions in medicinal and material chemistry. Extension of substrate types from aromatic halides to other unconventional aromatic electrophiles is a highly important yet challenging task in catalytic methylation. Disclosed herein is a series of transitio...

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Detalles Bibliográficos
Autores principales: Feng, Boya, Yang, Yudong, You, Jingsong
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/PMC8159405/
https://www.ncbi.nlm.nih.gov/pubmed/34094095
http://dx.doi.org/10.1039/d0sc01641a
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author Feng, Boya
Yang, Yudong
You, Jingsong
author_facet Feng, Boya
Yang, Yudong
You, Jingsong
author_sort Feng, Boya
collection PubMed
description Methylation is one of the most fundamental conversions in medicinal and material chemistry. Extension of substrate types from aromatic halides to other unconventional aromatic electrophiles is a highly important yet challenging task in catalytic methylation. Disclosed herein is a series of transition metal-catalyzed methylations of unconventional inert aryl electrophiles using trimethylboroxine (TMB) as the methylating reagent. This transformation features a broad substrate type, including nitroarenes, benzoic amides, benzoic esters, aryl cyanides, phenol ethers, aryl pivalates and aryl fluorides. Another important merit of this work is that these widespread “inert” functionalities are capable of serving as directing or activating groups for selective functionalization of aromatic rings before methylation, which greatly expands the connotation of methylation chemistry.
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spelling pubmed-81594052021-06-04 A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent Feng, Boya Yang, Yudong You, Jingsong Chem Sci Chemistry Methylation is one of the most fundamental conversions in medicinal and material chemistry. Extension of substrate types from aromatic halides to other unconventional aromatic electrophiles is a highly important yet challenging task in catalytic methylation. Disclosed herein is a series of transition metal-catalyzed methylations of unconventional inert aryl electrophiles using trimethylboroxine (TMB) as the methylating reagent. This transformation features a broad substrate type, including nitroarenes, benzoic amides, benzoic esters, aryl cyanides, phenol ethers, aryl pivalates and aryl fluorides. Another important merit of this work is that these widespread “inert” functionalities are capable of serving as directing or activating groups for selective functionalization of aromatic rings before methylation, which greatly expands the connotation of methylation chemistry. The Royal Society of Chemistry 2020-05-25 /pmc/articles/PMC8159405/ /pubmed/34094095 http://dx.doi.org/10.1039/d0sc01641a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Feng, Boya
Yang, Yudong
You, Jingsong
A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent
title A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent
title_full A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent
title_fullStr A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent
title_full_unstemmed A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent
title_short A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent
title_sort methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8159405/
https://www.ncbi.nlm.nih.gov/pubmed/34094095
http://dx.doi.org/10.1039/d0sc01641a
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