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 ...
