Parameters Influencing Reactivity and Regioselectivity in the Methoxycarbonylation of Arylalkenes

Maretha du Plessis; Charlene Marais; Barend C. B. Bezuidenhoudt

doi:10.1055/s-0035-1560912

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(04): 557-565
DOI: 10.1055/s-0035-1560912

paper

Parameters Influencing Reactivity and Regioselectivity in the Methoxycarbonylation of Arylalkenes

Maretha du Plessis

Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa eMail: bezuidbc@ufs.ac.za

,

Charlene Marais

Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa eMail: bezuidbc@ufs.ac.za

,

Barend C. B. Bezuidenhoudt*

Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa eMail: bezuidbc@ufs.ac.za

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Abstract

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Abstract

Previous research showed that the steric bulk, electronic character, and bite angle of the ligand have an influence on both the catalyst activity and regioselectivity of hydroformylation and hydroesterification reactions. However, little is known in this regard about the influence of the steric and electronic environment around the double bond of the substrate. A variety of arylalkenes were therefore subjected to methoxycarbonylation to investigate the steric and electronic effects of substituents on the aromatic ring of the substrate on the regioselectivity and reactivity in the methoxycarbonylation reaction of these substrates with a Pd(II)/Al(OTf)₃/Ph₃P catalyst system.

Key words

hydroesterification - arylalkenes - palladium - aluminum triflate - regioselectivity

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Referenzen

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