Synthesis 2016; 48(04): 557-565
DOI: 10.1055/s-0035-1560912
paper
© Georg Thieme Verlag Stuttgart · New York

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: [email protected]
,
Charlene Marais
Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa   Email: [email protected]
,
Barend C. B. Bezuidenhoudt*
Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 15 September 2015

Accepted after revision: 12 October 2015

Publication Date:
25 November 2015 (online)


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.

Supporting Information

 
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