Oxidative Arylation of Ethylene with Benzene to Produce Styrene

Matsumoto, Takaya; Yoshida, Hajime

doi:10.1246/cl.2000.1064

Cited by 85 publications

(32 citation statements)

References 12 publications

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“…The catalytic oxidative phenylation of ethylene to produce styrene is achieved more effectively with rhodium complexes (Scheme 9) [42,43]. A mixture of 1.0 mM of Rh(acac)(CO) 2 (acac = acetylacetonate), benzene, and acetylacetone was pressurized with ethylene and O 2 then heated at 180 ºC [42].…”

Section: Methodsmentioning

confidence: 99%

Developments in Catalytic Aromatic C-H Transformations: Promising Tools for Organic Synthesis

Goj¹,

Gunnoe²

2005

COC

107

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Catalytic carbon-carbon bond formation using transition metal complexes typically incorporates the use of an aryl halide or triflate compound (electrophile) in combination with an organometallic reagent (nucleophile). Versatile synthetic methods that allow C-C bond formation of aromatic compounds that proceed through transformation of C-H bonds would be of substantial value. Potential routes for C-C bond formation with aromatic substrates include the hydroarylation of unsaturated compounds (e.g., olefins or alkynes) and oxidative coupling of aromatic compounds and olefins or alkynes. Such reactions can proceed through metal-mediated transformation of C-H bonds. The range of reported catalysts and catalytic cycles for these classes of reactions have been reviewed herein. X = Me (70 %), OMe (73 %), Cl (74 %), Br (49 %) X OEt O X OEt O Pd(OAc) 2 (7 mol %) H 4 PMo 11 V 1 O 40 90 o C, O 2 (1 atm) + Developments in Catalytic Aromatic C-H Transformations Current

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Section: Methodsmentioning

confidence: 99%

Developments in Catalytic Aromatic C-H Transformations: Promising Tools for Organic Synthesis

Goj¹,

Gunnoe²

2005

COC

107

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“…Promising results were also reported with heteropolyoxometalates as co-catalysts [14,15,[17][18][19]. While there is considerable effort focused on designing highly active homogeneous systems, there are no reports on heterogeneous catalysts.…”

Section: Methodsmentioning

confidence: 99%

Heterogeneous alkenylation of aromatics under oxygen

Hájek¹,

Dams²,

Detrembleur³

et al. 2007

Catalysis Communications

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A novel heterogeneous Pd/polymer catalyst containing co-catalytic functional groups catalyses the direct alkenylation of anisole with ethyl trans-cinnamate under oxygen. The properties of the polymeric catalyst were compared to other immobilised catalysts. The activity of the polymeric catalyst typically increased with temperature and oxygen pressure exhibiting the optimal activity up to 100 TON at 383 K under 1. 2 MPa of O 2 . The most abundant product was 3-(p-methoxyphenyl)-3-phenylpropanoate (≈45%). The reaction selectivity was practically independent of the conditions. Split-tests and AAS measurements confirm heterogeneous character of the catalyst.

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“…[79] 2011 berichteten Glorius und Mitarbeiter über die Rh-katalysierte Kupplung von Bromaromaten mit Styrolen zu meta-u nd para-Produkten (7d) unter sterischer Kontrolle.W enn 1,2-und 1,3-disubstituierte Aromaten verwendet wurden, konnten olefinierte Arene wie 7e und 7ferhalten werden (Schema 8). [79] 2011 berichteten Glorius und Mitarbeiter über die Rh-katalysierte Kupplung von Bromaromaten mit Styrolen zu meta-u nd para-Produkten (7d) unter sterischer Kontrolle.W enn 1,2-und 1,3-disubstituierte Aromaten verwendet wurden, konnten olefinierte Arene wie 7e und 7ferhalten werden (Schema 8).…”

Section: Alkenylierung/olefinierungunclassified