Nickel-catalyzed remote and proximal Wacker-type oxidation

• DOI: 10.1038/s42004-018-0107-y
• Publication Date: 2019-01-04T12:02:22Z
• Authors: Binbin Liu; Penghui Hu; Fangning Xu; Lu Cheng; Mingxi Tan; Wei Han
• Keywords: Wacker process; Commodity chemicals

Abstract Wacker oxidation chemistry is widely applied to of olefins carbonyls in the synthesis pharmaceuticals, natural products, and commodity chemicals. However, this efficient internal highly selective unbiased without reliance upon suitable coordinating groups have remained significant challenges. Here we report a nickel-catalyzed remote Wacker-type where reactions occur at less-reactive sp 3 C–H sites presence priori more reactive ones through chain-walking mechanism with excellent regio- chemo- selectivity. This transformation has attractive features including use ambient air as sole oxidant, naturally-abundant nickel catalyst, polymethylhydrosiloxane hydride source room temperature, allowing for effective challenging olefins. Notably, approach enables direct access broad array complex, medicinally relevant molecules from structurally complex substrates chemical feedstocks.