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Synthesis of Sulfones from Organozinc Reagents, DABSO, and Alkyl Halides

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journal contribution
posted on 03.01.2014, 00:00 by Benjamin N. Rocke, Kevin B. Bahnck, Michael Herr, Sophie Lavergne, Vincent Mascitti, Christian Perreault, Jana Polivkova, Andrei Shavnya
Organozinc reagents react with the SO2 surrogate DABSO, and the resulting zinc sulfinate salts are alkylated in situ to afford sulfones. This transformation has a broad scope and is compatible with a wide range of structural motifs of medicinal chemistry relevance including nitrile, secondary carbamates, and nitrogen-containing heterocycles.