Diazonium Salts as Substrates in Palladium-Catalyzed Cross-Coupling Reactions

Roglans, Anna; Pla‐Quintana, Anna; Moreno-Mañas‡, § Marcial

doi:10.1021/cr0509861

Cited by 754 publications

(319 citation statements)

References 121 publications

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“…Since the early reports by Suzuki and Miyaura on the cross-coupling reaction a tremendous development has taken place in terms of substrate flexibility and reaction conditions. A range of different catalysts and conditions are now available for the successful cross-coupling of halides, triflates, O-tosylates, and diazonium salts upon reaction with boronic acid, boronates, and trifluoroborates [3,7,[11][12][13][14][15]]. …”

Section: Introductionmentioning

confidence: 99%

The Use of Palladium on Magnetic Support as Catalyst for Suzuki–Miyaura Cross-Coupling Reactions

Sydnes

2017

Catalysts

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Abstract:The development of new solid supports for palladium has received a lot of interest lately. These catalysts have been tested in a range of cross-coupling reactions, such as Suzuki-Miyaura, Mizoroki-Heck, and Sonogashira cross-coupling reactions, with good outcomes. Attaching the catalyst to a solid support simplifies the operations required in order to isolate and recycle the catalyst after a reaction has completed. Palladium on solid supports made of magnetic materials is particularly interesting since such catalysts can be removed very simply by utilizing an external magnet, which withholds the catalyst in the reaction vessel. This review will showcase some of the latest magnetic solid supports for palladium and highlight these catalysts' performance in Suzuki-Miyaura cross-coupling reactions.

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Section: Introductionmentioning

confidence: 99%

The Use of Palladium on Magnetic Support as Catalyst for Suzuki–Miyaura Cross-Coupling Reactions

Sydnes

2017

Catalysts

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“…Different methods allow the reactions to be performed under safer conditions, with no need for the isolation of diazonium species, for example, the in situ generation of diazonium salts from free anilines (with catalytic or stoichiometric amounts of acid) or the use of aryltriazenes as latent diazonium salts. Both pre-formed [13][14][15] and in situ generated [16] diazonium salts have been used in palladium-catalyzed crosscoupling reactions. The copper-mediated Sandmeyer reaction, disclosed more than a century ago, [17] was first performed under catalytic conditions by Beletskaya et al using phenanthroline as ligand.…”

Section: Introductionmentioning

confidence: 99%

Antagonistic Effect of Acetates in C–N Bond Formation with In Situ Generated Diazonium Salts: A Combined Theoretical and Experimental Study

et al. 2016

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“…However, Heck arylations employing arenediazonium salts as electrophiles have received relatively less attention in comparison to the more traditional aryl halide-or triflate-based arylation protocols. 4 Yet, arenediazonium salts offer several economical, environmental and practical advantages over aryl halides. Arenediazonium salts are easily prepared, are often less expensive than the aryl halides, provide faster palladiumcatalyzed arylation reactions, are used under phosphinefree conditions and allow more user-friendly open-air experimental conditions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel room temperature chiral ionic liquids: application as reaction media for the heck arylation of aza-endocyclic acrylates

Pastre¹,

Génisson²,

Saffon³

et al. 2010

J. Braz. Chem. Soc.

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Novos líquidos iônicos aquirais e quirais foram preparados utilizando-se rotas sintéticas inéditas e/ou otimizadas. Estas séries de líquidos iônicos do tipo imidazolínico, imidazólico e piridínico foram totalmente caracterizadas, incluindo-se análises por calorimetria diferencial de varredura (DSC). O desempenho desses líquidos iônicos (LIs) foi demonstrado empregando-se a arilação de Heck de aza-acrilato endocíclicos com sais de arenodiazônio ou iodetos de arila. As arilações de Heck realizadas na presença destas entidades iônicas quirais, seja como um solvente ou um aditivo, foram eficazes levando à completa conversão do substrato, em bons a excelentes rendimentos do aduto de Heck na maioria dos casos, apesar de não ser observada indução assimétrica em nenhum dos casos estudados. Dois novos complexos quirais de paládio do tipo carbeno N-heterocíclico foram preparados em bons rendimentos a partir de um sal imidazólico quiral e suas estruturas caracterizadas por difração de raios-X. De modo geral, a arilação de Heck empregando tetrafluoroboratos de arenodiazônio em líquidos iônicos demonstrou ser mais eficiente do que os protocolos tradicionais em termos de reatividade e rendimentos de reação.New achiral and chiral RTILs were prepared using novel and/or optimized synthetic routes. These new series of imidazolinium, imidazolium, pyridinium and nicotine-derived ionic liquids were fully characterized including differential scanning calorimetry (DSC) analysis. The performance of these achiral and chiral room temperature ionic liquids (RTILs) was demonstrated by means of the Heck arylation of endocyclic acrylates employing arenediazonium salts and aryl iodides. The Heck arylations performed in the presence of these ionic entities, either as a solvent or as an additive, were effective leading to complete conversion of the substrate and good to excellent yield of the Heck adduct. In spite of the good performances, no asymmetric induction was observed in any of the cases studied. Two new diastereoisomeric NHC-palladium complexes were prepared in good yields from a chiral imidazolium salt and their structure characterized by X-ray diffraction. Overall, the Heck arylations employing arenediazonium tetrafluoroborates in RTILs were more effective than the traditional protocols employing aryl iodides in terms of reactivity and yields.

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Diazonium Salts as Substrates in Palladium-Catalyzed Cross-Coupling Reactions

Cited by 754 publications

References 121 publications

The Use of Palladium on Magnetic Support as Catalyst for Suzuki–Miyaura Cross-Coupling Reactions

The Use of Palladium on Magnetic Support as Catalyst for Suzuki–Miyaura Cross-Coupling Reactions

Antagonistic Effect of Acetates in C–N Bond Formation with In Situ Generated Diazonium Salts: A Combined Theoretical and Experimental Study

Synthesis of novel room temperature chiral ionic liquids: application as reaction media for the heck arylation of aza-endocyclic acrylates

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