A Practical Protocol for the Hiyama Cross-Coupling Reaction Catalyzed by Palladium on Carbon

Monguchi, Yasunari; Yanase, Takayoshi; Mori, Shigeki; Sajiki, Hironao

doi:10.1055/s-0032-1316801

Cited by 25 publications

(16 citation statements)

References 5 publications

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“…Various biaryl compounds have been synthesized using this protocol [Eq. (19)] ,. Moreover, the same group found that this catalytic system still works when the tris(4‐fluorophenyl)phosphine is replaced by acetic acid.…”

Section: Applications Of Pd/cmentioning

confidence: 99%

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Liu

Astruc

2018

Adv Synth Catal

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Palladium on charcoal( Pd/C)h as lots of salient merits:( i) it is ac heap andc ommercial source of palladium, (ii)i ts hows efficientc atalytic activity even without ligands,( iii)a saheterogeneous catalyst it is easily recycledm any times by simple filtration,a nd (iv) it is applicablet oag reat number of reactions and substrates,a lthough it is eventually less efficient than homogeneous Pd catalysts containing some sophisticated ligands.T hisr eview recalls the main background ands ummarizes the progress made essentially during the last twelve years in Pd/C-catalyzed organic synthesis since the reviews by Felpins group andSekiin2 006.

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Section: Applications Of Pd/cmentioning

confidence: 99%

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Liu

Astruc

2018

Adv Synth Catal

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“…In this way, a facile bond breaking of the carbon-silicon bond during transmetalation is favored. It was demonstrated that alkali metal salt such as NaF or CsF could also act as silane activators for Hiyama coupling reactions (Gurung et al 2013;Monguchi et al 2012). In addition, both ammonium-and phosphonium-based ionic liquid have been proved to be good extractants of Pd suggesting their complexing ability (Katsuta et al 2011;Regel-Rosocka et al 2015).…”

Section: Resultsmentioning

confidence: 99%

Tetrabutylphosphonium 4-ethoxyvalerate as a biomass-originated media for homogeneous palladium-catalyzed Hiyama coupling reactions

et al. 2020

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The introduction of a biomass-derived ionic liquid into the Hiyama coupling reactions, which has been considered as a powerful tool for the synthesis of symmetrically and non-symmetrically substituted biaryl structures, could further control or even reduce the environmental impact of this transformation. It was shown that tetrabutylphosphonium 4-ethoxyvalerate, a γ-valerolactone-based ionic liquid, can be utilized as an alternative solvent to create carbon–carbon bonds between aryl iodides and functionalized organosilanes in the presence of 1 mol% Pd under typical Hiyama conditions (130 °C, 24 h, tetrabutylammonium fluoride activator). A comparison of different ionic liquids was performed, and the effects of the catalyst precursor and the moisture content of the reaction mixture on the activity of the catalyst system were investigated. The functional group tolerance was also studied, resulting in 15 cross-coupling products (3a–o) with isolated yields of 45–72% and excellent purity (> 98%).

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“…Preparation of new molecules with improved properties is of current importance. Therefore, including halides in the aromatic system, in particular iodine, results in very important intermediates for the synthesis of more complicated molecules, since it allows a wide range of reactions such as Sonogashira, 24 Suzuki, 25 Stille, 26 Heck, 27 Hiyama, 28 Negishi, 29 etc. Preparation of compounds with groups such as iodine are of a high synthetic value and a wide variety of reactions can be performed.…”

Section: Resultsmentioning

confidence: 99%

Improved Method for Microwave-Assisted Synthesis of Benzodiazepine-2,5-diones from Isatoic Anhydrides Mediated by Glacial Acetic Acid

Cruz¹,

Vega-Acevedo²,

Rivero³

et al. 2018

J. Braz. Chem. Soc.

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An improved and simpler method for the synthesis of benzodiazepin-2,5-diones and 7-iodobenzodiazepin-2,5-diones catalyzed by glacial acetic acid using isatoic anhydride and 6-iodoisatoic anhydride, respectively, as starting materials is reported. The target products were achieved in good yields (up to 71%) using microwave irradiation as the activating mode of reaction in the presence of acetic acid instead of the traditional polar aprotic solvents as dimethylformamide (DMF), dimethyl sulfoxide (DMSO) or dimethylacetamide (DMAC). Moreover, relatively simple purification workup is required. The optimal temperature to obtain the benzodiazepin-2,5-dione derivatives was 130 °C, while the best irradiation time was 3 min. In addition, the methodology for the selective preparation of 6-iodoisatoic anhydride with an overall yield of 62% is presented.

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A Practical Protocol for the Hiyama Cross-Coupling Reaction Catalyzed by Palladium on Carbon

Cited by 25 publications

References 5 publications

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Tetrabutylphosphonium 4-ethoxyvalerate as a biomass-originated media for homogeneous palladium-catalyzed Hiyama coupling reactions

Improved Method for Microwave-Assisted Synthesis of Benzodiazepine-2,5-diones from Isatoic Anhydrides Mediated by Glacial Acetic Acid

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