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Synfacts 2009(1): 0075-0075  
DOI: 10.1055/s-0028-1087446
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Improved Synthesis of gem-Diiodoalkanes

Contributor(s): Paul Knochel, Andrei Gavryushin
J. A. Bull, A. B. Charette*
Université de Montréal, Canada
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Publikationsverlauf

Publikationsdatum:
18. Dezember 2008 (online)

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Significance

gem-Diiodoalkanes are useful precursors in several organic transformations like Simmons-Smith cyclopropanation and Takai olefination. This method allows a convenient preparation of gem-diiodides by the alkylation of diiodo­methyl anion with alkyl iodides or benzylic and allylic bromides. A broad functional group tolerance is demonstrated for this reaction.