Bromination of enamines from tertiary amides using the petasis reagent: A convenient one-pot regioselective route to bromomethyl ketones

Article abstract of DOI:10.1080/00397911.2013.765484

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%). Mechanistic details and optimum conditions for the reaction are briefly discussed. The present approach offers several advantages such as regioselectivity in enamine formation, good yields, mild reaction conditions, and ease of experimentation.

Full text of DOI:10.1080/00397911.2013.765484

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Edited by Jonathan L Sessler and Philip A Gale
ISSN: 1061-0278
Volume 23 Numbers 9–10 September–October 2011
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Jonathan L. Sessler
Philip A. Gale
School of Chemistry,
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Southampton, UK
The University of Texas at Austin,
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