Abstract
New, improved phosphine ligands for palladium-catalyzed butadiene telomerization with methanol have been discovered. Using high throughput experimentation and an Electrospray Ionization-Mass Spectrometry (ESI-MS) investigation of telomerization catalysts solutions, we have identified phosphines of the type P(C 6H 4-2-OMe) 2(C 6H 5−n(X) n), where X is an electron-withdrawing group, as high selectivity, high activity phosphine ligands for butadiene telomerization with methanol to 1-methoxy-2,7-octadiene (MOD-1). These ligands were designed to mitigate anaerobic oxidation of phosphines by alkylation which was shown by Electrospray Ionization-Mass Spectrometry (ESI-MS) studies to correlate with catalyst death and palladium precipitation in working telomerization catalyst solutions. The best phosphine-promoted catalysts achieve selectivities to desired 1-methoxy-2,7-octadiene of 94% at high butadiene conversion, significantly improved over those achieved commercially by triphenylphosphine.
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