Aryl a-diimine derivatives have been used, for the first time, as efficient new ligands for the palladium-catalyzed oxidative bis-alkoxycarbonylation reaction of olefins. The most active catalyst wasformed in situ from bis(9-anthryl)-2,3-dimethyl-1,4-diazabutadiene and palladium(II) trifluoroacetate [Pd(TFA) 2]. This catalytic system was able to selectively convert olefins into succinic diesters in goodyields (up to 97%) and low catalyst loading (up to 0.5 mol%) under mild reaction conditions [4 bar of carbon monoxide (CO) at 20 °C in the presence ofptoluenesulphonic acid as additive and p-benzoquinone as oxidant] . The optimized conditions could be successfully applied to both aromatic and aliphatic olefins, by using methanol, benzyl alcohol or isopropyl alcohol as nucleophiles.
Selective Aryl a-Diimmine/Palladium-Catalyzed Bis-Alkoxycarbonylation of Olefins for the Synthesis of Substituted Succinic Diesters
CARFAGNA, CARLA
2014
Abstract
Aryl a-diimine derivatives have been used, for the first time, as efficient new ligands for the palladium-catalyzed oxidative bis-alkoxycarbonylation reaction of olefins. The most active catalyst wasformed in situ from bis(9-anthryl)-2,3-dimethyl-1,4-diazabutadiene and palladium(II) trifluoroacetate [Pd(TFA) 2]. This catalytic system was able to selectively convert olefins into succinic diesters in goodyields (up to 97%) and low catalyst loading (up to 0.5 mol%) under mild reaction conditions [4 bar of carbon monoxide (CO) at 20 °C in the presence ofptoluenesulphonic acid as additive and p-benzoquinone as oxidant] . The optimized conditions could be successfully applied to both aromatic and aliphatic olefins, by using methanol, benzyl alcohol or isopropyl alcohol as nucleophiles.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
