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Issue 29, 2014
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The metal tin promoted cascade reaction of ketones in aqueous media for the construction of 2-bromo-4-aryl-1,3-pentadiene

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Abstract

A novel type of transformation was discovered serendipitously during the Barbier-type allenylation reaction of aromatic ketones promoted by the metal, tin, in aqueous media. Additionally, a series of new, highly functionalized 2-bromo-4-aryl-1,3-pentadienes could be obtained with good yields in this reaction. This cascade reaction shows the unique properties of the metal, tin. Furthermore, it is actually a cascade reaction which involves two steps: one is the Barbier-type allenylation of the carbonyl compound, and the other is an SN2′ type addition–elimination reaction. Notably, this reaction has the advantages of simple, mild conditions and is easy to operate. Furthermore, the corresponding product could be applied to various coupling reactions or other diversified transformations.

Graphical abstract: The metal tin promoted cascade reaction of ketones in aqueous media for the construction of 2-bromo-4-aryl-1,3-pentadiene

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Publication details

The article was received on 20 Mar 2014, accepted on 28 Apr 2014 and first published on 28 Apr 2014


Article type: Paper
DOI: 10.1039/C4OB00584H
Citation: Org. Biomol. Chem., 2014,12, 5393-5399
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    The metal tin promoted cascade reaction of ketones in aqueous media for the construction of 2-bromo-4-aryl-1,3-pentadiene

    L. Liu, Y. Zhang, H. Zhang, K. Huang, B. Gao, M. Zou, X. Zhou, H. Wang and J. Li, Org. Biomol. Chem., 2014, 12, 5393
    DOI: 10.1039/C4OB00584H

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