Mild and chemoselective synthesis of lactones from diols using a novel metal-ligand bifunctional catalyst.
[reaction: see text] A novel amino alcohol-based Ir bifunctional complex acts as an efficient catalyst for oxidative lactonization of 1,4- or 1,5-diols with a substrate-to-catalyst molar ratio of 200-1000 in acetone or butanone. The reaction proceeds with broad functional group tolerance to give lactone in high yield at room temperature. The catalyst precursor Cp*IrCl[OCH(2)C(C(6)H(5))(2)NH(2)] is isolated and characterized by a single-crystal X-ray analysis.
Suzuki
Takeyuki
T
Department of Synthetic Organic Chemistry, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi 981-8558, Japan.
Morita
Kenji
K
Tsuchida
Mika
M
Hiroi
Kunio
K
D002384:Catalysis; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D007495:Iridium / Q000737:chemistry; D007659:Ketones; D007783:Lactones / Q000138:chemical synthesis*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008670:Metals; D008958:Models, Molecular; D010084:Oxidation-Reduction
D007202:Indicators and Reagents; D007659:Ketones; D007783:Lactones; D008024:Ligands; D008670:Metals; D007495:Iridium