Hydroesterification of Vinylarenes Catalyzed by Palladium Complexes of Dialkylmonoaryl- and Monoalkyldiarylphosphines

Yasutoyo Kawashima, Kentaro Okano, Kyoko Nozaki, Tamejiro Hiyama

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

Hydroesterification of vinylarenes using a mixture of PdCl2 and monodentate phosphorus ligands as a catalyst was studied. As ligands, menthyldiphenylphosphine (MDPP), neomenthyldiphenylphosphine (NMDPP), and dicyclohexyl(phenyl)phosphine (Cy2PPh) were effective to obtain branched esters with high regioselectivity under the moderate reaction conditions without additives such as acids. Not only electronic effects but also steric effects of the cycloalkyl groups were revealed to be significant in order to achieve high catalytic activity. When (S)-2-dicyclopentylphosphino-2′-methoxy-1,1′-binaphthyl was used for the asymmetric hydroesterification of 2-methoxy-6-vinylnaphthalene, (S)-naproxen methyl ester was obtained with 53% ee.

Original languageEnglish
Pages (from-to)347-355
Number of pages9
JournalBulletin of the Chemical Society of Japan
Volume77
Issue number2
DOIs
Publication statusPublished - 2004 Feb 1

ASJC Scopus subject areas

  • Chemistry(all)

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