Electroreductive crossed pinacol coupling of aromatic ketones with aliphatic ketones and aldehydes |
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Authors: | Naoki Kise Yousuke Shiozawa Nasuo Ueda |
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Affiliation: | Department of Biotechnology, Faculty of Engineering, Tottori University, Koyama, Tottori 680-8552, Japan |
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Abstract: | The intermolecular crossed pinacol coupling of aromatic ketones with aliphatic aldehydes and ketones was effected by electroreduction in the presence of chlorotrimethylsilane. The best result was obtained using a Pb cathode in Bu4NPF6/THF. The electroreduction of aromatic 1,4-, 1,5-, and 1,6-diketones under the same conditions gave four-, five-, and six-membered 1,2-diols with trans-stereoselectivity, while the reduction of these diketones with TiCl4-Zn produced the cis-isomers of the same intramolecular crossed pinacol coupling products predominantly. |
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