Using Aryl Diazonium Salts in Palladium-Catalyzed Reactions under Safer Conditions

Oger, Nicolas; d’Halluin, Martin; Grognec, Erwan Le; Felpin, François‐Xavier

doi:10.1021/op500299t

Cited by 119 publications

(80 citation statements)

References 87 publications

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“…To circumvent this issue, the multicomponent synthesis of 1,2,3-triazoles involving the generation of organic azides in situ from organic halides and sodium azide has been first proposed by Fokin and Van der Eycken. [82,83] In continuation of our research interest in the development of methodologies involving very reactive intermediates in safe conditions, [84,85] we investigated the multicomponent synthesis of 1,2,3-triazoles using Cu…”

Section: Catalyst Activitymentioning

confidence: 99%

Graphite-supported ultra-small copper nanoparticles – Preparation, characterization and catalysis applications

d’Halluin

Mabit

Fairley

et al. 2015

Carbon

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Section: Catalyst Activitymentioning

confidence: 99%

Graphite-supported ultra-small copper nanoparticles – Preparation, characterization and catalysis applications

d’Halluin

Mabit

Fairley

et al. 2015

Carbon

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“…Along with problems arising due to the high reactivity of the aryl radical intermediates, an additional challenge is the handling of the potentially unstable aryl diazonium precursors. Although these high energy species are routinely handled on large scale, [29][30][31][32] safety concerns 33 still inhibit their adoption among the wider synthetic community.…”

Section: Introductionmentioning

confidence: 99%

Retraction of “Ascorbic Acid-Promoted C–H Arylation of Heterocyclic N-Oxides through in Situ Diazotisation of Anilines: A Green and Selective Coupling Process”

Colleville¹,

Horan²,

Olazabal³

et al. 2015

Org. Process Res. Dev.

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A green and selective method for the generation of heterocyclic bi-aryl compounds through C-H arylation of heterocyclic N-oxides is presented in which ascorbic acid acts as the sole promoter for both the in-situ generation of an aryldiazonium species and the subsequent arylation. Reaction conditions were optimised through Multivariate Data Analysis and Design of Experiments methodologies resulting in further sustainability improvements, and were then applied to a range of substrates to establish the scope and limitations of the new methodology. This reaction was ultimately performed on a multigram scale and subjected to reaction calorimetry studies to support further scale-up and identify opportunities to elucidate the mechanistic course of this metal-free transformation.

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“…The Mizoroki-Heck reactions have exhibited good functional group tolerance with a wide range of substrates under mild conditions. At present, not only aryl, vinyl, benzyl, and alkyl halides [1][2][3][4][5][6], but also the corresponding pseudo halides such as sulfonates [10][11][12], sulfonyl chlorides [13][14][15], carboxylic acid derivatives [16][17][18], diazonium salts [19][20][21], iodonium salts [22,23], phosphonium salts [24], and sulfonium salts [25], have been successfully employed as electrophiles in Heck-type cross-couplings. Both electron-poor and -rich alkenes (such as acrylic esters, enolethers, and ethylene) have proved to be viable cross-coupling partners in the reactions [1][2][3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Pd-Catalyzed Mizoroki-Heck Reactions Using Fluorine-Containing Agents as the Cross-Coupling Partners

Yang

Zhao

et al. 2018

Catalysts

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Abstract:The Mizoroki-Heck reaction represents one of the most convenient methods for carbon-carbon double bond formation in the synthesis of small organic molecules, natural products, pharmaceuticals, agrochemicals, and functional materials. Fluorine-containing organic compounds have found wide applications in the research areas of materials and life sciences over the past several decades. The incorporation of fluorine-containing segments into the target molecules by the Mizoroki-Heck reactions is highly attractive, as these reactions efficiently construct carbon-carbon double bonds bearing fluorinated functional groups by simple procedures. This review summarizes the palladium-catalyzed Mizoroki-Heck reactions using various fluorine-containing reagents as the cross-coupling partners. The first part of the review describes the Pd-catalyzed Mizoroki-Heck reactions of aryl halides or pseudo-halides with the fluorinated alkenes, and the second part discusses the Pd-catalyzed Mizoroki-Heck reactions of the fluorinated halides or pseudo-halides with alkenes. Variants of the Pd-catalyzed Mizoroki-Heck reactions with fluorine-containing reagents are also briefly depicted. This work supplies an overview, as well as a guide, to both younger and more established researchers in order to attract more attention and contributions in the realm of Mizoroki-Heck reactions with fluorine-containing participants.

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Using Aryl Diazonium Salts in Palladium-Catalyzed Reactions under Safer Conditions

Cited by 119 publications

References 87 publications

Graphite-supported ultra-small copper nanoparticles – Preparation, characterization and catalysis applications

Graphite-supported ultra-small copper nanoparticles – Preparation, characterization and catalysis applications

Retraction of “Ascorbic Acid-Promoted C–H Arylation of Heterocyclic N-Oxides through in Situ Diazotisation of Anilines: A Green and Selective Coupling Process”

Pd-Catalyzed Mizoroki-Heck Reactions Using Fluorine-Containing Agents as the Cross-Coupling Partners

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