Oxidative Generation of α-Radicals of Carbonyl Compounds from the α-Stannyl Derivatives and Their Reactions with Electron-Rich Olefins

Article abstract of DOI:10.1246/bcsj.68.322

The oxidation of α-tributylstannyl alkanoates with tetrabutylammonium hexanitratocerate(IV) generates α-radicals of the alkanoates by eliminating the stannylium ion.The thus-formed radicals react with various electron-rich olefinic compounds, such as silyl enol ethers, giving addition products in good yield.This method formally achieves selective cross coupling between alkanoates and ketones.