Synthetic Communications

Bromination of Enamines from Tertiary Amides Using the Petasis Reagent: A Convenient One-Pot Regioselective Route to Bromomethyl Ketones

M Kobeissi, K Cherry, W Jomaa

Index: Kobeissi, Marwan; Cherry, Khalil; Jomaa, Wissam Synthetic Communications, 2013 , vol. 43, # 21 p. 2955 - 2965

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Citation Number: 2

Abstract

An original one-pot synthesis of bromomethyl ketones is achived using the Petasis reagent (dimethyltitanocene) as a key for enamine generation. Several amides were used to test the limits of the procedure by changing either the alkyl chain R or the amino portion of the starting materials. The enamines generated in situ were allowed to react with bromine at low temperature followed by hydrolysis to yield bromomethyl ketones in excellent yields (85 to 95%). ...