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Jenna L. Jeffrey, Emily S. Bartlett and Prof. Richmond Sarpong Intramolecular C(sp3)[BOND]N Coupling by Oxidation of Benzylic C,N-Dianions Angewandte Chemie International Edition 52

Version of Record online: 16 JAN 2013 | DOI: 10.1002/anie.201209591

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What a couple! An intramolecular, C(sp3)[BOND]N coupling to afford azacycles is reported. This reaction proceeds through the oxidation of benzylic C,N-dianions with iodine and builds on an earlier discovery during the synthesis of the natural product lyconadin A. The current study employs conformationally unbiased substrates with less acidic C[BOND]H bonds and less reactive nitrogen nucleophiles. ZnCl2 was identified as an important additive.

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