Efficient heterogeneous vinylation of aryl halides using potassium vinyltrifluoroborate

Joucla, Lionel; Cusati, Giuseppe; Pinel, Catherine; Djakovitch, Laurent

doi:10.1016/j.tetlet.2008.05.119

Cited by 34 publications

(8 citation statements)

References 19 publications

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“…), Pd/C (0.1 mol%), NMP, 100 8C]. [26,27] Complete conversion of 3-bromoquinoline was observed after 16 h and 3-vinylquinoline was directly subjected to Heck coupling. Addition of 3-chloroiodobenzene in excess (i.e., 2.0 equiv.)…”

Section: Resultsmentioning

confidence: 99%

“…[26,27] Such compounds are useful intermediates for the synthesis of stilbenes, an important class of biologically relevant molecules including the wellknown resveratrol and combretastatin A-4. [28,29] Over the past few years, three reports dealing with homogenous Pd-based one-pot strategies, through either Hiyama/Heck [30] or double Heck [31,32] couplings, have emerged from the literature as valuable improvements toward the synthesis of stilbenes.…”

Section: Introductionmentioning

confidence: 99%

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One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

et al. 2010

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Joucla, Lionel Cusati, Giuseppe Pinel, Catherine Djakovitch, LaurentThe synthesis of (E)-stilbenes was performed following a one-pot Suzuki/Heck sequence through the use of potassium vinyltrifluoroborate. The combination of heterogeneous palladium/silica (Pd/SiO2) catalyst with potassium phosphate monohydrate (K3PO4H2O) as base resulted in useful to good isolated yields regardless of the ortho-, meta- or para-substitution of the aryl halides employed. In a sustainable approach. we found that bio-sourced 1,3-propanediol could advantageously replace N-methyl-pyrrolidone (NMP) as similar yields were obtained Moreover, the reactivity gap between aryl iodides and bromides resulting from the use of 1,3-propanediol allowed an efficient multi-component approach toward the synthesis of (E)-stilbenes. Furthermore. this heterogeneous catalyst was found to he extremely robust despite the use of aerobic conditions and was successfully re-used over several cycles

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

et al. 2010

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“…16 The study of Suzuki reactions in water or aqueous-organic mixtures has received much attention since then. [17][18][19][20][21][22][23] Due to the ability to dissolve bases in water for activating arylboronic acids, the reaction proceeds much faster in an aqueous medium. Zhang et al reported that the palladium-catalyzed Suzuki reaction of aryl bromides with arylboronic acids occurred smoothly in aqueous acetone 24 or PEG/H 2 O 25 in the absence of a ligand.…”

Section: Introductionmentioning

confidence: 99%

A simple and efficient protocol for a palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF

Bao

et al. 2011

Green Chem.

113

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A convenient, effective and mild protocol has been developed for the palladium-catalyzed ligand-free Suzuki reaction of aryl bromides with arylboronic acids in aqueous N,N-dimethylformamide (DMF) in the presence of K 2 CO 3 and a catalytic amount of PdCl 2 in air at room temperature. It is noteworthy that the volume ratio of water-DMF and base play important roles in the reaction, and various functional groups are tolerated under the optimized conditions. Furthermore, this protocol could be extended to the cross-couplings of nitrogen-based heteroaryl halides with arylboronic acids in moderate to excellent yields.

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“…Adopting the described procedure, we evaluated the cross-coupling with PdCl 2 /PPh 3 , Pd(OAc) 2 /PPh 3 , Pd(PPh 3 ) 4 [17] and Pd/C. [18] The reaction proceeded well and full conversion was achieved in all cases using 2 mol-% of Pd source, 3 equiv. of Cs 2 CO 3 as base and THF/H 2 O (9:1) as solvent under microwave irradiation at 100°C and a maximum power of 200 W (Table 3).…”

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confidence: 99%

Microwave‐Assisted Palladium‐Catalyzed Heterogeneous Vinylation of 2(1H)‐Pyridones

Singh¹,

Cavalluzzo²,

Maeyer³

et al. 2009

Eur J Org Chem

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Efficient heterogeneous vinylation of aryl halides using potassium vinyltrifluoroborate

Cited by 34 publications

References 19 publications

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

A simple and efficient protocol for a palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF

Microwave‐Assisted Palladium‐Catalyzed Heterogeneous Vinylation of 2(1H)‐Pyridones

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