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Novel ultra-small Pd NPs on SOS spheres: a new catalyst for domino intramolecular Heck and intermolecular Sonogashira couplings

We report a novel catalyst Pd/SOS that catalyzes the dual C–C bond forming coupling of an iodoarene moiety with an internal alkene and an external alkyne via an intramolecular Heck reaction, followed by an intermolecular Sonogashira reaction, respectively. The catalyst was characterized using XRD, I...

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Autores principales: Lakshminarayana, Bhairi, Vinodkumar, T., Satyanarayana, G., Subrahmanyam, Ch.
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/PMC9049139/
https://www.ncbi.nlm.nih.gov/pubmed/35495233
http://dx.doi.org/10.1039/c9ra09429f
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author Lakshminarayana, Bhairi
Vinodkumar, T.
Satyanarayana, G.
Subrahmanyam, Ch.
author_facet Lakshminarayana, Bhairi
Vinodkumar, T.
Satyanarayana, G.
Subrahmanyam, Ch.
author_sort Lakshminarayana, Bhairi
collection PubMed
description We report a novel catalyst Pd/SOS that catalyzes the dual C–C bond forming coupling of an iodoarene moiety with an internal alkene and an external alkyne via an intramolecular Heck reaction, followed by an intermolecular Sonogashira reaction, respectively. The catalyst was characterized using XRD, IR, XPS, SEM and TEM analyses. Notably, for the first time, cheap and readily available new silica [nanosilica on microsilica (SOS)] material-supported ultra-small Pd nanoparticles (2.20 nm) are employed for the efficient synthesis of dihydrobenzofuran and oxindole derivatives in a domino one-pot reaction. Significantly, a sub-molar quantity of Pd (0.3 mol%) was found to be sufficient to furnish the products in very good to near quantitative yields. Gratifyingly, the catalyst could be recycled up to five cycles with a marginal loss (∼no loss) of the product.
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spelling pubmed-90491392022-04-29 Novel ultra-small Pd NPs on SOS spheres: a new catalyst for domino intramolecular Heck and intermolecular Sonogashira couplings Lakshminarayana, Bhairi Vinodkumar, T. Satyanarayana, G. Subrahmanyam, Ch. RSC Adv Chemistry We report a novel catalyst Pd/SOS that catalyzes the dual C–C bond forming coupling of an iodoarene moiety with an internal alkene and an external alkyne via an intramolecular Heck reaction, followed by an intermolecular Sonogashira reaction, respectively. The catalyst was characterized using XRD, IR, XPS, SEM and TEM analyses. Notably, for the first time, cheap and readily available new silica [nanosilica on microsilica (SOS)] material-supported ultra-small Pd nanoparticles (2.20 nm) are employed for the efficient synthesis of dihydrobenzofuran and oxindole derivatives in a domino one-pot reaction. Significantly, a sub-molar quantity of Pd (0.3 mol%) was found to be sufficient to furnish the products in very good to near quantitative yields. Gratifyingly, the catalyst could be recycled up to five cycles with a marginal loss (∼no loss) of the product. The Royal Society of Chemistry 2020-01-28 /pmc/articles/PMC9049139/ /pubmed/35495233 http://dx.doi.org/10.1039/c9ra09429f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Lakshminarayana, Bhairi
Vinodkumar, T.
Satyanarayana, G.
Subrahmanyam, Ch.
Novel ultra-small Pd NPs on SOS spheres: a new catalyst for domino intramolecular Heck and intermolecular Sonogashira couplings
title Novel ultra-small Pd NPs on SOS spheres: a new catalyst for domino intramolecular Heck and intermolecular Sonogashira couplings
title_full Novel ultra-small Pd NPs on SOS spheres: a new catalyst for domino intramolecular Heck and intermolecular Sonogashira couplings
title_fullStr Novel ultra-small Pd NPs on SOS spheres: a new catalyst for domino intramolecular Heck and intermolecular Sonogashira couplings
title_full_unstemmed Novel ultra-small Pd NPs on SOS spheres: a new catalyst for domino intramolecular Heck and intermolecular Sonogashira couplings
title_short Novel ultra-small Pd NPs on SOS spheres: a new catalyst for domino intramolecular Heck and intermolecular Sonogashira couplings
title_sort novel ultra-small pd nps on sos spheres: a new catalyst for domino intramolecular heck and intermolecular sonogashira couplings
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9049139/
https://www.ncbi.nlm.nih.gov/pubmed/35495233
http://dx.doi.org/10.1039/c9ra09429f
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