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Synfacts 2010(3): 0345-0345  
DOI: 10.1055/s-0029-1219311
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

SmI2/H2O/Amine Promoted Cleavage of Benzyl-Heteroatom Bonds

Contributor(s): Paul Knochel, Andreas J. Wagner
T. Ankner, G. Hilmersson*
University of Gothenburg, Göteborg, Sweden
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

A variety of benzylic amines, alcohols, esters, and benzenethiol have been found to undergo a radical defunctionalization reaction when treated with aqueous SmI2 in the presence of a base. The corresponding alkylarenes are ­obtained in excellent yields.