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Alkaline-earth-based catalysts for C–C bond formation

By Edited by Gerald Ondrey |

Salts of alkaline-earth metals have been shown to catalyze reactions for the selective formation of carbon-carbon bonds, by chemistry professor Shu Kobayashi and colleagues at the University of Tokyo (www.chem.s.u-tokyo.ac.jp). The research, supported by the Japan Science and Technology Agency (Tokyo), promises to deliver alternatives to conventional catalysts that contain toxic, scarce and expensive metals. The researchers found that alkaline-earth-metal salts can activate, with an atomic efficiency of 100%, the nucleating agent sulfonyl imidate, which enables them to selectively form C–C bonds. Futhermore, Kobayashi’s group has shown that the stereoselectivity can be adjusted by using different solvents. For example, the Mannich reaction of benzaldehyde-derived imine and sulfonyl imidate results in a 94% yield with a syn-to-anti ratio of 4-to-96 after 17 h, when performed with 10 mol% Mg(OtBu)2, in dimethyl formaldehyde solvent at room temperature (OtBu = tert-butoxy). Switching to 10 mol% of Sr(HMDS)2 (with 11 % ligand) and THF (tetrahydrofuran) solvent (HMDS = hexamethyldisilazide), the Mannich reaction leads to a 92% yield after 24 h, with syn-to-anti ratio of 93-to-7. The group has confirmed that it can select anti-…
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