NDLI: Room-Temperature, Ligand- and Base-Free Heck Reactions of Aryl Diazonium Salts at Low Palladium Loading: Sustainable Preparation of Substituted Stilbene Derivatives

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Room-Temperature, Ligand- and Base-Free Heck Reactions of Aryl Diazonium Salts at Low Palladium Loading: Sustainable Preparation of Substituted Stilbene Derivatives

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Felpin, François-xavier Laudien, Julia Miqueu, Karinne Fouquet, Eric Sotiropoulos, Jean-marc Ibarguren, Oier
Description	Author Affiliation: Felpin FX ( Université de Bordeaux, CNRS-UMR 5255, Institut des Sciences Moléculaires (ISM), 351, Cours de la Libération, Talence, 33405 France. fx.felpin@ism.u-bordeaux1.fr)
Abstract	The $Pd(OAc)_{2}-catalyzed$ Heck reaction of aryl diazonium salts with 2-arylacrylates led to cis-stilbenes with good to excellent stereoselectivity. The environmentally friendly protocol developed in this work features low palladium loading in technical-grade methanol at room temperature under base-, additive-, and ligand-free conditions. The same protocol applied to simple Heck coupling of aryl diazonium salts with methyl acrylate allows astonishingly low palladium loading, down to 0.005 mol %. The stereoselectivity experimentally observed for the synthesis of cis-stilbenes has been rationalized by DFT calculations. Moreover, the role of methanol in promoting the reaction has been clarified by a computational study.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	17
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-05-03
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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Heck Reactions of Aryl Chlorides Catalyzed by Ligand Free Palladium Salts

Palladium-Catalysed Desulfitative Heck Reaction Tolerant to Aryl Carbon-Halogen Bonds for Access to (Poly)halo-Substituted Stilbene or Cinnamate Derivatives

Bimetallic Substituted Ceria: An Alternative Approach to Ligand-Free Heck-Mizoroki Cross-Coupling Reactions

Direct C3-Arylation of 2H-Indazole Derivatives with Aryl Bromides by using Low Loading of a Phosphine-free Palladium Catalyst

Sustainable Heck–Matsuda Reaction with Catalytic Amounts of Diazonium Salts: An Experimental and Theoretical Study

Heterogeneously catalyzed phosphine-free heck cross-coupling reaction of aryl halides with reusable palladium(II) schiff base complex

A palladium salen complex: an efficient catalyst for the Sonogashira reaction at room temperature

Palladium-catalyzed heck-type arylation of acrylate with diaryliodonium salts

Ligand-free heck coupling and homocoupling of aryl halides in the presence of tetrabutylammonium nitrate

Room-Temperature, Ligand- and Base-Free Heck Reactions of Aryl Diazonium Salts at Low Palladium Loading: Sustainable Preparation of Substituted Stilbene Derivatives

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Room-Temperature, Ligand- and Base-Free Heck Reactions of Aryl Diazonium Salts at Low Palladium Loading: Sustainable Preparation of Substituted Stilbene Derivatives