Reaction of aryl di-, tri-, or tetrabromides with arylboronic acids or alkenes in the presence of a palladium-tetraphosphine catalyst

Berthiol, Florian; Kondolff, Isabelle; Doucet, Henri; Santelli, Maurice

doi:10.1016/j.jorganchem.2004.06.007

Cited by 39 publications

(16 citation statements)

References 71 publications

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“…All compounds are determined by MS analysis and obtained results were compared with these published in the references [70][71][72][73][74][75][76][77][78][79][80][81][82]. …”

Section: One-pot Reaction Of Oxidative Heck and Heck Reactionmentioning

confidence: 99%

Oxygen-promoted coupling of arylboronic acids with olefins catalyzed by [CA]2[PdX4] complexes without a base

Silarska

Trzeciak

2015

Journal of Molecular Catalysis A: Chemical

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a b s t r a c tAn efficient method was developed for the oxidative Heck reaction between arylboronic acids and olefins catalyzed by anionic palladium complexes of the type [CA] x [PdCl 4 ] (x = 1,2) and [CA] 2 [Pd 2 Cl 6 ] (CA = imidazolium or pyridinium cation). Molecular oxygen was employed as an environmentally benign oxidant to regenerate Pd(II) species during the reaction. The elaborated protocol could be applied to the coupling of different arylboronic acids with both electron-rich and electron-poor olefins. The catalyst system was further employed for the one-pot oxidative Heck reaction followed by the Heck coupling to build conjugated compounds in good yield.Mass spectrometry (ESI-MS) and UV-vis spectroscopy was used to identify palladium-containing complexes in the reactions. A plausible reaction mechanism of the oxidative Heck reaction was proposed.

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“…All compounds are determined by MS analysis and obtained results were compared with these published in the references [70][71][72][73][74][75][76][77][78][79][80][81][82]. …”

Section: One-pot Reaction Of Oxidative Heck and Heck Reactionmentioning

confidence: 99%

Oxygen-promoted coupling of arylboronic acids with olefins catalyzed by [CA]2[PdX4] complexes without a base

Silarska

Trzeciak

2015

Journal of Molecular Catalysis A: Chemical

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“…The mixture was then heated to 90 8 8C. [144] Scheme 30 Palladium-Catalyzed Heck Reactions with 3,4-Dibromothiophene [144] Ph 5000:1 0:100 20 [144] 3-Tol 250:1 100:0 78 [144] 3-ClC 6 H 4 250:1 100:0 80 [144] a Conditions: DMF, 130 8 8C. The organic phases were combined and the product was isolated by vacuum distillation; yield: 117 g (91%).…”

Section: S Brmentioning

confidence: 99%

“…Dibutyl (2E,2¢E)-3,3¢-(Thiophene-3,4-diyl)diacrylate (69,R 1 =CO 2 Bu); Typical Procedure: [144] The reaction of 3,4-dibromothiophene (68; 0.242 g, 1.00 mmol), butyl acrylate (0.512 g, 4.00 mmol), and K 2 CO 3 (4.00 mmol) at 130 Palladium-containing nanostructured silica 71 bearing trialkyl(4-pyridyl)ammonium binding sites can be used as a heterogeneous catalyst for Heck coupling reactions. This methodology is especially useful because of the easy recovery and reuse of the catalyst.…”

Section: S Brmentioning

confidence: 99%

Thiophenes, Thiophene 1,1-Dioxides, and Thiophene 1-Oxides (Update 2011)

Carreira¹,

Drabowicz²,

Fuerstner³

et al. 2011

Knowledge Updates 2011/2

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“…[27,28] The reaction with 1,4-dibromobenzene gives the corresponding p-terphenyl with excellent conversion and selectivity after 1 h (entry 2, Table 2); in addition, the process gives ca 9% of biphenyl by effect of a homocoupling reaction. Based on the variation of the product concentrations with time, the coupling reaction takes place in a consecutive manner, first at a bromine atom and then at the other; in fact, as can be seen from Fig.…”

Section: Suzuki Reaction Of Phenyl Polybromidesmentioning

confidence: 99%

Suzuki cross‐coupling reaction of aryl and heterocyclic bromides and aromatic polybromides on a Pd(II)‐hydrotalcite catalyst

Mora¹,

Jiménez‐Sanchidrián²,

Ruíz³

2008

Applied Organom Chemis

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The Suzuki cross-coupling reaction of various bromine-containing substrates and phenylboronic acid in toluene at 90• C on a Pd(AcO) 2 Py 2 catalyst supported on an Mg-Al hydrotalcite, using K 2 CO 3 as the base, was studied. The conversion and selectivity results obtained for many of the substrates were excellent and similar to those provided by more active or even homogeneous catalysts. The reactions of aryl polybromides and phenylboronic acid gave the corresponding polyaromatic compounds in variable yields depending on the particular substrate. Arylation occurred in a consecutive manner by substitution of the different Br atoms. ICP-MS measurements of the palladium content of the catalyst performed prior to and after the reaction revealed that part of the metal is incorporated into the bulk solution; therefore, the catalytic process is not purely heterogeneous.

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Reaction of aryl di-, tri-, or tetrabromides with arylboronic acids or alkenes in the presence of a palladium-tetraphosphine catalyst

Cited by 39 publications

References 71 publications

Oxygen-promoted coupling of arylboronic acids with olefins catalyzed by [CA]2[PdX4] complexes without a base

Oxygen-promoted coupling of arylboronic acids with olefins catalyzed by [CA]2[PdX4] complexes without a base

Thiophenes, Thiophene 1,1-Dioxides, and Thiophene 1-Oxides (Update 2011)

Suzuki cross‐coupling reaction of aryl and heterocyclic bromides and aromatic polybromides on a Pd(II)‐hydrotalcite catalyst

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