Nikel-Catalyzed Enantioselective C(sp3)-H Arylation of Ketones with Aryl Ethers via Selective CAr-O Cleavage to Construct All-Carbon Quaternary Stereocenters

Abstract

We designed thenickel-catalyzed enantioselective C(sp3)-H arylation of ketones with phenol-derived aryl pyrimidyl ethers via selective cleavage of the C(aryl)-O bond to construct all-carbon quaternary stereocenters. This method exhibits good functional group compatibility and broad substrate scope. Drug molecule donepezil can directly transform into corresponding highly optically pure derivatives with this developedmethodology. Mechanistic studies reveal that C(aryl)-O cleavage of aryl pyrimidyl ether probably proceeded by means of an anionic organo-Ni(0) intermediate.