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Open AccessFeature PaperArticle

A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water

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Institut Galien Paris-Sud, CNRS UMR 8612, Université Paris-Saclay, Faculté de Pharmacie, 5 rue JB Clément, 92296 Châtenay-Malabry, France
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Institut de Chimie Moléculaire et des Matériaux d’Orsay, CNRS UMR 8182, Université Paris Saclay, Bâtiment 420, 91405 Orsay, France
3
NOVECAL, 86 rue de Paris, 91400 Orsay, France
*
Authors to whom correspondence should be addressed.
Academic Editor: Yves Canac
Molecules 2020, 25(6), 1459; https://doi.org/10.3390/molecules25061459
Received: 9 March 2020 / Revised: 20 March 2020 / Accepted: 22 March 2020 / Published: 24 March 2020
(This article belongs to the Special Issue Carbon Ligands: From Fundamental Aspects to Applications)
Nanoformulated calix[8]arenes functionalized with N-heterocyclic carbene (NHC)-palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol arylborates at low temperature in water without any organic co-solvent. Combined with an improved one-step synthesis of triol arylborates from boronic acid, this remarkably efficient new tool provided a variety of 4′-arylated phenylalanines and tyrosines in good yields at low catalyst loading with a wide functional group tolerance. View Full-Text
Keywords: NHC; nanoparticle; calixarene; palladium catalyst; Suzuki-Miyaura reaction; amino-acids; water NHC; nanoparticle; calixarene; palladium catalyst; Suzuki-Miyaura reaction; amino-acids; water
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Peramo, A.; Abdellah, I.; Pecnard, S.; Mougin, J.; Martini, C.; Couvreur, P.; Huc, V.; Desmaële, D. A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water. Molecules 2020, 25, 1459.

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