Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction

Herein we report a mild synthesis of propargyl silanes from terminal alkynes. We exploit a bromonaphthyl-substituted silane as a silylmethyl electrophile surrogate, which participates in a Sonogashira reaction after an aryl-to-alkyl Pd-migration. Twenty-seven propargyl silanes were obtained in up to...

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Detalles Bibliográficos
Autores principales: Puriņš, Mikus, Eichenberger, Lucas, Waser, Jérôme
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10286695/
https://www.ncbi.nlm.nih.gov/pubmed/37272881
http://dx.doi.org/10.1039/d3cc01847d
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author Puriņš, Mikus
Eichenberger, Lucas
Waser, Jérôme
author_facet Puriņš, Mikus
Eichenberger, Lucas
Waser, Jérôme
author_sort Puriņš, Mikus
collection PubMed
description Herein we report a mild synthesis of propargyl silanes from terminal alkynes. We exploit a bromonaphthyl-substituted silane as a silylmethyl electrophile surrogate, which participates in a Sonogashira reaction after an aryl-to-alkyl Pd-migration. Twenty-seven propargyl silanes were obtained in up to 88% yield. The obtained products were versatile building blocks that can be used in addition to electrophiles, triple bond hydrogenation or silyl group cleavage with acid or fluoride sources.
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spelling pubmed-102866952023-06-23 Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction Puriņš, Mikus Eichenberger, Lucas Waser, Jérôme Chem Commun (Camb) Chemistry Herein we report a mild synthesis of propargyl silanes from terminal alkynes. We exploit a bromonaphthyl-substituted silane as a silylmethyl electrophile surrogate, which participates in a Sonogashira reaction after an aryl-to-alkyl Pd-migration. Twenty-seven propargyl silanes were obtained in up to 88% yield. The obtained products were versatile building blocks that can be used in addition to electrophiles, triple bond hydrogenation or silyl group cleavage with acid or fluoride sources. The Royal Society of Chemistry 2023-05-31 /pmc/articles/PMC10286695/ /pubmed/37272881 http://dx.doi.org/10.1039/d3cc01847d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Puriņš, Mikus
Eichenberger, Lucas
Waser, Jérôme
Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction
title Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction
title_full Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction
title_fullStr Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction
title_full_unstemmed Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction
title_short Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction
title_sort synthesis of propargyl silanes from terminal alkynes via a migratory sonogashira reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10286695/
https://www.ncbi.nlm.nih.gov/pubmed/37272881
http://dx.doi.org/10.1039/d3cc01847d
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