Letters in Organic Chemistry [ Diethylzinc-Mediated Allylation of Natural Biphenyls by  -1,1- Dimethyleneallylpalladium Complexes ]

Maria   Antonietta   Dettori; Jean      Ollivier; Pier   Paolo   Piras; Davide      Fabbri; Giovanna      Delogu; Jacques      Salaun

doi:10.2174/1570178053765384

Abstract

1-Ethenylcyclopropyl sulfonate underwent electrophilic γ- and α-substitutions by the carbonyls of naturally occurring biphenyls derived from vanillin and acetovanillone, in the presence of palladium(0) and diethylzinc, to provide regioisomeric 5,5-di(3-cyclopropylidene-1-hydroxypropyl) biphenyls and 5,5-di[1-(1-ethenylcyclopropyl)-1-hydroxymethyl]biphenyls of biological interest.

Keywords: dimethyleneallylzinc complex, palladium, electrophilic additions, biaryls, allylations

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Letters in Organic Chemistry

Title: Letters in Organic Chemistry [ Diethylzinc-Mediated Allylation of Natural Biphenyls by -1,1- Dimethyleneallylpalladium Complexes ]

Volume: 2 Issue: 3

Author(s): Maria Antonietta Dettori, Jean Ollivier, Pier Paolo Piras, Davide Fabbri, Giovanna Delogu and Jacques Salaun

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Keywords: dimethyleneallylzinc complex, palladium, electrophilic additions, biaryls, allylations

Abstract: 1-Ethenylcyclopropyl sulfonate underwent electrophilic γ- and α-substitutions by the carbonyls of naturally occurring biphenyls derived from vanillin and acetovanillone, in the presence of palladium(0) and diethylzinc, to provide regioisomeric 5,5-di(3-cyclopropylidene-1-hydroxypropyl) biphenyls and 5,5-di[1-(1-ethenylcyclopropyl)-1-hydroxymethyl]biphenyls of biological interest.

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Dettori Antonietta Maria, Ollivier Jean, Piras Paolo Pier, Fabbri Davide, Delogu Giovanna and Salaun Jacques, Letters in Organic Chemistry [ Diethylzinc-Mediated Allylation of Natural Biphenyls by -1,1- Dimethyleneallylpalladium Complexes ], Letters in Organic Chemistry 2005; 2 (3) . https://dx.doi.org/10.2174/1570178053765384