Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP

• DOI: 10.1021/acs.orglett.9b00031
• Publication Date: 2019-01-18T13:02:59Z
• Authors: Shuang-Qi Tang; Jacques Bricard; Martine Schmitt; Frédéric Bihel
• Keywords: Natural product; Environmentally Friendly; Coupling reaction

An efficient and user-friendly palladium(II) precatalyst, POxAP (post-oxidative-addition precatalyst), was identified for use in Fukuyama cross-coupling reactions. Suitable storage under air, the precatalyst allowed reaction between thioesters organozinc reagents with turnover numbers of ∼90000. A series 23 ketones were obtained yields ranging from 53 to 99%. As proof efficacy, an alternative approach developed synthesis a key precursor natural product isoprekinamycin.