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Carbonylation of benzyl bromide to benzeneacetatic acid and its esters catalysed by water-soluble palladium complexes.

Autorzy

Anna M. Trzeciak

Józef J. Ziółkowski

Rok wydania

2000

Czasopismo

Journal of Molecular Catalysis A-Chemical

Numer woluminu

154

Strony

93-101

DOI

10.1016/S1381-1169(99)00390-8

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

A catalytic system containing PdCl2(cod) (cod=1,5-cyclooctadiene) and a water-soluble phosphine PNS (PNS=Ph2PCH2CH2C(O)NHC(CH3)2CH2SO3Li) in water/toluene solution exhibits activity in the carbonylation of benzyl bromide to benzeneacetic acid (87% yield) at 130°C and 10 atm of CO. In a reaction carried out in water/alcohol solution, corresponding esters were obtained in yields dependent on the kind of alcohol used: 24% for BuOH, 62% for iPrOH, 78% for EtOH, and 85% for MeOH. In the synthesis of benzeneacetic acid methyl ester C6H5CH2C(O)OCH3 at 50–100°C under 5–10 atm of CO, TOF ca. 300 was achieved. The contribution of palladium(0) phosphine complexes was proved using the 31P{1H} NMR and IR methods. The complex Pd(PNS)4, obtained in the reaction of PdCl2(cod) with PNS and NaBH4, reacts with C6H5CH2Br yielding an oxidative addition product, PdBr(C6H5CH2)(PNS)2, identified using the 31P{1H} NMR method. In CD3OD solution containing Pd(PNS)4 and C6H5CH2Br saturated with CO, the ester described by the formula C6H5CH2C(O)OCD3 was identified. This suggests that the reaction of CO-insertion into PdC bonding is relatively fast.

Słowa kluczowe

Palladium, Water soluble catalyst, Carbonylation, Benzyl bromide, Benzeneacetic acid

Adres publiczny

https://doi.org/10.1016/S1381-1169(99)00390-8

Strona internetowa wydawcy

http://www.elsevier.com

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