A versatile ketone formation via highly active precatalyst “ poxap ” : application to the synthesis of isoprekinamycin

Shuang-Qi Tang,Jacques Bricard, Martine Schmitt, Frédéric Bihel


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A series of efficient and user-friendly palladium(II) precatalysts named “POxAPs” (post-oxidative-addition precatalyst) were identified for use in Fukuyama cross-coupling reaction. These POxAPs, of generic formula PdX(Ar)(PPh3)2, can be easily prepared from the oxidative addition of Pd(0) with ArX, and stored under air at ambient temperature. With turnover number of ∼90 000, 10 ppm of POxAP are enough to catalyze the reaction between thioesters and organozinc reagents to afford a large diversity of ketones with yields up to 99%. This method was particularly efficient for the synthesis of very bulky ketones. As proof of efficacy, an alternative approach was developed for the synthesis of a key precursor of the natural product isoprekinamycin.
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