New trialkylsilyl enol ether chemistry: direct 1,2-bis-azidonation of triisopropylsilyl enol ethers: an azido-radical addition process promoted by TEMPO

Treatment of triisopropylsilyl enol ethers with PhIO/TMSN3/TEMPO (cat.)–45 °C results in 1,2-bis-azidonation, which appears to occur through a radical addition process; the 1-azido group can be replaced by carbon nucleophiles such as allyl, methyl, cyano, acetylene and acetonyl.