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A bi-metallic nanocluster catalyst for highly selective asymmetric C–C formation

By Tetsuo Satoh |

Shu Kobayashi and his research group at the University of Tokyo (Japan; www.chem.s.u-tokyo.ac.jp/users/synorg/index_e.html) have developed a ruthenium-silver nanocluster catalyst for the highly selective 1,4-addition reaction for the formation of asymmetric carbon-carbon bonds. Previously, the group had used its polymeric incarceration (PI) method to form metallic nanoclusters supported on a polystyrene-based polymeric matrix. Now, a very robust, highly selective catalyst has been developed with Rh-Ag nanoclusters supported on PI and carbon black (PI/CB Rh/Ag), which has been shown to be effective for the asymmetric 1,4-addition of arylboronic acids to enones. The use of carbon black as a secondary support enhances the specific surface area, while Ag suppresses coagulation of Rh. The catalyst is less prone to leaching of metals (below detection limits) than predecessors, and can be recycled several times while maintaining high yields and excellent enantioselectivities, says Kobayashi. In laboratory trials, asymmetric C–C bond-formation products were obtained from the reaction of cyclohexenone and phenyl boronic acid, using a toluene-water solvent. A 99% yield with enantioselectivity of 98% was achieved using PI/CB Rh/Ag after…
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