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Titanocene-catalysed, selective reduction of ketones in aqueous media. A safe, mild, inexpensive procedure for the synthesis of secondary alcohols via radical chemistry

Abstract:

We report here a novel procedure for the reduction of ketones to secondary alcohols using catalytic quantities of commercially available Cp2TiCl2, inexpensive Zn dust and water as proton source. Mechanistically the reaction presumably proceeds via titanoxy radicals. In practice this reduction process has significant advantages: it shows an interesting selectivity pattern, takes place under mild conditions using safe, cheap reagents and does not require anhydrous solvents. The proton-donor activity of water under these conditions avoids the use of the frequently poisonous hydrogen-atom donors generally required to reduce free radicals. This procedure is also highly convenient for synthesising deuterium-labelled alcohols employing relatively inexpensive D2O as deuterium source. © 2003 Elsevier Science Ltd. All rights reserved.