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Highly Selective Radical Monoreduction of Dihalides Confined to a Dynamic Supramolecular Host |
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| Authors: | Dr Manuel Petroselli Prof Julius Rebek Jr Prof Yang Yu |
| Institution: | 1. Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science, Shanghai University, 99 Shang-Da Road, Shanghai, 200444 P. R. China;2. The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute for Chemical Biology and Department of Chemistry, 10550 North Torrey Pines Road, La Jolla, California, 92037 USA |
| Abstract: | Reduction of alkyl dihalide guests ( 2 – 5 and 7 ) with trialkylsilanes (R3SiH) was performed in water-soluble host 1 to investigate the effects of confinement on fast radical reactions (k≥103 m −1 s−1). High selectivity (>95 %) for mono-reduced products was observed for primary and secondary dihalide guests under mild conditions. The results highlight the importance of host–guest complexation rates to modulate the product selectivity in radical reactions. |
| Keywords: | dynamic host free radicals radical reduction supramolecular chemistry water-soluble cavitand |