Tetrahedron

Electroreductive crossed pinacol coupling of aromatic ketones with aliphatic ketones and aldehydes

N Kise, Y Shiozawa, N Ueda

Index: Kise, Naoki; Shiozawa, Yousuke; Ueda, Nasuo Tetrahedron, 2007 , vol. 63, # 25 p. 5415 - 5426

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Citation Number: 18

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 ...