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Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C–Cl site

This study described palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates in the Ar–Cl bond. The Pd/SelectPhos system showed excellent chemoselectivity toward the Ar–Cl bond in the presence of the Ar–OTf bond with a broad substrate scope and excellent...

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Autores principales: Chen, Zicong, Gu, Changxue, Yuen, On Ying, So, Chau Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9067565/
https://www.ncbi.nlm.nih.gov/pubmed/35655875
http://dx.doi.org/10.1039/d1sc06701j
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author Chen, Zicong
Gu, Changxue
Yuen, On Ying
So, Chau Ming
author_facet Chen, Zicong
Gu, Changxue
Yuen, On Ying
So, Chau Ming
author_sort Chen, Zicong
collection PubMed
description This study described palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates in the Ar–Cl bond. The Pd/SelectPhos system showed excellent chemoselectivity toward the Ar–Cl bond in the presence of the Ar–OTf bond with a broad substrate scope and excellent product yields. The electronic and steric hindrance offered by the –PR(2) group of the ligand with the C2-alkyl group was found to be the key factor affecting the reactivity and chemoselectivity of the α-arylation reaction. The chemodivergent approach was also successfully employed in the synthesis of flurbiprofen and its derivatives (e.g., –OMe and –F).
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spelling pubmed-90675652022-06-01 Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C–Cl site Chen, Zicong Gu, Changxue Yuen, On Ying So, Chau Ming Chem Sci Chemistry This study described palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates in the Ar–Cl bond. The Pd/SelectPhos system showed excellent chemoselectivity toward the Ar–Cl bond in the presence of the Ar–OTf bond with a broad substrate scope and excellent product yields. The electronic and steric hindrance offered by the –PR(2) group of the ligand with the C2-alkyl group was found to be the key factor affecting the reactivity and chemoselectivity of the α-arylation reaction. The chemodivergent approach was also successfully employed in the synthesis of flurbiprofen and its derivatives (e.g., –OMe and –F). The Royal Society of Chemistry 2022-03-16 /pmc/articles/PMC9067565/ /pubmed/35655875 http://dx.doi.org/10.1039/d1sc06701j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Chen, Zicong
Gu, Changxue
Yuen, On Ying
So, Chau Ming
Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C–Cl site
title Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C–Cl site
title_full Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C–Cl site
title_fullStr Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C–Cl site
title_full_unstemmed Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C–Cl site
title_short Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C–Cl site
title_sort palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the c–cl site
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9067565/
https://www.ncbi.nlm.nih.gov/pubmed/35655875
http://dx.doi.org/10.1039/d1sc06701j
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