Aryl Diazonium <i>versus</i> Iodonium Salts: Preparation, Applications and Mechanisms for the Suzuki–Miyaura Cross‐Coupling Reaction

Bonin, Hélène; Fouquet, Éric; Felpin, François‐Xavier

doi:10.1002/adsc.201100531

Cited by 127 publications

(60 citation statements)

References 120 publications

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“…Heck reactions using arene diazonium salts were pioneered by Matsuda and coworkers in the late 1970's, and are therefore referred to as Matsuda–Heck reactions . Over the past decade, the progress in this field has been documented in several reviews …”

Section: Introductionmentioning

confidence: 99%

Styrylsulfonates and ‐Sulfonamides through Pd‐Catalysed Matsuda–Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts

2016

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Arene diazonium salts undergo Matsuda-Heck reactions with vinylsulfonates and -sulfonamides to give styrylsulfonic acid derivatives in high to excellent yields and with high to excellent selectivities. By quantifying the evolution of nitrogen over time in a gas-meter apparatus, the reactivities of ethylvinylsulfonate and the benchmark olefin methyl acrylate were compared for an electron-rich and an -deficient arene diazonium salt. Tertiary sulfonamides react in Matsuda-Heck couplings with high conversions, but require long reaction

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Section: Introductionmentioning

confidence: 99%

Styrylsulfonates and ‐Sulfonamides through Pd‐Catalysed Matsuda–Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts

2016

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“…The Suzuki–Miyaura reaction is arguably one of the most practiced methods for carbon–carbon bond formation 1. Whereas most studies employ aryl halides or triflates as electrophilic partners, aryl diazonium salts have been reported to be excellent surrogates for various palladium‐catalyzed reactions,2 including Suzuki‐type cross‐couplings 3. 4 Thereby, these “super‐electrophiles”, readily prepared from inexpensive anilines, compete favorably with less reactive and more expensive aryl halides or triflates.…”

Section: Introductionmentioning

confidence: 99%

Chelation‐Assisted Cross‐Coupling of Anilines through In Situ Activation as Diazonium Salts with Boronic Acids under Ligand‐, Base‐, and Salt‐Free Conditions

Joncour

Susperrégui

Pinaud

et al. 2013

Chemistry A European J

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We describe the coupling of anilines with aryl boronic acids, under ligand-, base-, and salt-free conditions at room temperature. This new reaction proceeds through the formation of an aryl palladium alkoxo complex, which allows the transmetalation step with aryl boronic acids without any external base. Importantly, this sustainable procedure generates only environmentally friendly byproducts such as tBuOH, H2O, N2, and B(OH)3. The reaction mechanism has been deeply investigated through experimental and theoretical studies.

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“…Temperature was ever kept at 4°C due to the well-known thermal lability of the diazonium compounds with chloride as a counterion (Bonin et al 2011). …”

Section: Optimization Of Reaction Conditionsmentioning

confidence: 99%

Diazo Coupling Reaction of Catechins and Alkylresorcinols with Diazotized Sulfanilic Acid for Quantitative Purposes in Edible Sources: Method Development and Validation

et al. 2015

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Catechins and alkylresorcinols are important secondary metabolites distributed in food products, sometimes exploited in quality control and/or as markers. The current methods for their quantitative analysis have some disadvantages such as cost, time consuming, and even insensitive or non-selective. Therefore, suitable, efficient methods are still required. As part of our research on new and rapid methods of analyses in plant and food products, a spectrophotometric method to quantify alkylresorcinols and catechins in plant products was developed and fully validated. The colored product by the diazo coupling between olivetol and catechin with diazotized sulfanilic acid was employed to develop the method. The effect of acid and diazonium salt concentration and the reaction time was analyzed. The method was linear in 0.8-8.3 and 0.6-10.2 μg/mL ranges to olivetol and catechin, respectively. Limit of detection and limit of quantification for olivetol and catechin were 0.253/0.768 and 0.106/0.321 μg/ mL, respectively. Precision at intra-day and inter-day levels (relative standard deviation (RSD) 1.3-9.7 %) and accuracy (99.0-104.9 %) were also demonstrated. Additionally, the application of the method to plant samples containing alkylresorcinol or catechins was subsequently evaluated, being comparable with conventionally employed methods. Thus, the method demonstrated to be fast, easy, inexpensive, and reliable for quantifying these kinds of metabolites in food products.

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Aryl Diazonium versus Iodonium Salts: Preparation, Applications and Mechanisms for the Suzuki–Miyaura Cross‐Coupling Reaction

Cited by 127 publications

References 120 publications

Styrylsulfonates and ‐Sulfonamides through Pd‐Catalysed Matsuda–Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts

Styrylsulfonates and ‐Sulfonamides through Pd‐Catalysed Matsuda–Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts

Chelation‐Assisted Cross‐Coupling of Anilines through In Situ Activation as Diazonium Salts with Boronic Acids under Ligand‐, Base‐, and Salt‐Free Conditions

Diazo Coupling Reaction of Catechins and Alkylresorcinols with Diazotized Sulfanilic Acid for Quantitative Purposes in Edible Sources: Method Development and Validation

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