Direct evidence of cis addition in the catalytic hydrocarboxylation of acenaphthylene to acenaphthene-1-carboxylic acid

Julio Real, Esther Prat, Sergio González-Cabello, Montserrat Pagès, Alfonso Polo

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10 Citations (Scopus)

Abstract

The hydrocarboxylation of acenaphthylene with the [PdCl2(CH3CN)2]+nPAr3 catalytic system gave good yields of acenaphthene-1-carboxylic acid, after it was found that the chemoselectivity over oligomeric side products is highly dependent on the electronic characteristics of the phosphine and the P/Pd ratio. Deuteriocarboxylation of this substrate has been found useful to determine the diastereoselectivity of this type of reaction, owing to the structure of the product. A series of results showed that hydrocarboxylation of acenaphthylene with oxalic acid and CO at 30 bar is highly diastereoselective in the cis isomer under all tested conditions but one.
Original languageEnglish
Pages (from-to)4715-4719
JournalOrganometallics
Volume19
Issue number23
DOIs
Publication statusPublished - 1 Nov 2000

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