A novel procedure for the synthesis of multifunctional ketones through the Fukuyama coupling reaction employing dialkylzincs

Treatment of thiol esters 1 with dialkylzincs 2 in the presence of zinc bromide, that was in situ prepared from zinc dust and bromine, provided various functionalized ketones 3 in high yields. The reaction mechanism, which may shift the Schlenk equilibrium from dialkylzincs 2 to reactive alkylzinc bromide 5, was postulated to account for the facile coupling reaction. (C) 2004 Elsevier Ltd. All rights reserved.