Synthesis of Benzothiophene-3-carboxylic Esters by Palladium Iodide-Catalyzed Oxidative Cyclization–Deprotection–Alkoxycarbonylation Sequence under Aerobic Conditions

[Image: see text] A palladium-catalyzed carbonylative approach to benzothiophene-3-carboxylic esters, starting from simple and readily available building blocks [2-(methylthio)phenylacetylenes, CO, an alcohol, and O(2) (from air)], is reported. The process is catalyzed by the simple PdI(2)/KI cataly...

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Autores principales: Mancuso, Raffaella, Cuglietta, Simona, Strangis, Romina, Gabriele, Bartolo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10127270/
https://www.ncbi.nlm.nih.gov/pubmed/35537181
http://dx.doi.org/10.1021/acs.joc.2c00686
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author Mancuso, Raffaella
Cuglietta, Simona
Strangis, Romina
Gabriele, Bartolo
author_facet Mancuso, Raffaella
Cuglietta, Simona
Strangis, Romina
Gabriele, Bartolo
author_sort Mancuso, Raffaella
collection PubMed
description [Image: see text] A palladium-catalyzed carbonylative approach to benzothiophene-3-carboxylic esters, starting from simple and readily available building blocks [2-(methylthio)phenylacetylenes, CO, an alcohol, and O(2) (from air)], is reported. The process is catalyzed by the simple PdI(2)/KI catalytic system to give the desired products in fair to high yields (57–83%). Interestingly, the reaction also works nicely in the ionic liquid BmimBF(4) as the solvent, with the possibility to recycle the catalytic system several times without appreciable loss of activity.
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spelling pubmed-101272702023-04-26 Synthesis of Benzothiophene-3-carboxylic Esters by Palladium Iodide-Catalyzed Oxidative Cyclization–Deprotection–Alkoxycarbonylation Sequence under Aerobic Conditions Mancuso, Raffaella Cuglietta, Simona Strangis, Romina Gabriele, Bartolo J Org Chem [Image: see text] A palladium-catalyzed carbonylative approach to benzothiophene-3-carboxylic esters, starting from simple and readily available building blocks [2-(methylthio)phenylacetylenes, CO, an alcohol, and O(2) (from air)], is reported. The process is catalyzed by the simple PdI(2)/KI catalytic system to give the desired products in fair to high yields (57–83%). Interestingly, the reaction also works nicely in the ionic liquid BmimBF(4) as the solvent, with the possibility to recycle the catalytic system several times without appreciable loss of activity. American Chemical Society 2022-05-10 /pmc/articles/PMC10127270/ /pubmed/35537181 http://dx.doi.org/10.1021/acs.joc.2c00686 Text en © 2022 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 Mancuso, Raffaella
Cuglietta, Simona
Strangis, Romina
Gabriele, Bartolo
Synthesis of Benzothiophene-3-carboxylic Esters by Palladium Iodide-Catalyzed Oxidative Cyclization–Deprotection–Alkoxycarbonylation Sequence under Aerobic Conditions
title Synthesis of Benzothiophene-3-carboxylic Esters by Palladium Iodide-Catalyzed Oxidative Cyclization–Deprotection–Alkoxycarbonylation Sequence under Aerobic Conditions
title_full Synthesis of Benzothiophene-3-carboxylic Esters by Palladium Iodide-Catalyzed Oxidative Cyclization–Deprotection–Alkoxycarbonylation Sequence under Aerobic Conditions
title_fullStr Synthesis of Benzothiophene-3-carboxylic Esters by Palladium Iodide-Catalyzed Oxidative Cyclization–Deprotection–Alkoxycarbonylation Sequence under Aerobic Conditions
title_full_unstemmed Synthesis of Benzothiophene-3-carboxylic Esters by Palladium Iodide-Catalyzed Oxidative Cyclization–Deprotection–Alkoxycarbonylation Sequence under Aerobic Conditions
title_short Synthesis of Benzothiophene-3-carboxylic Esters by Palladium Iodide-Catalyzed Oxidative Cyclization–Deprotection–Alkoxycarbonylation Sequence under Aerobic Conditions
title_sort synthesis of benzothiophene-3-carboxylic esters by palladium iodide-catalyzed oxidative cyclization–deprotection–alkoxycarbonylation sequence under aerobic conditions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10127270/
https://www.ncbi.nlm.nih.gov/pubmed/35537181
http://dx.doi.org/10.1021/acs.joc.2c00686
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