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Intramolecular C(sp 3 )N Coupling by Oxidation of Benzylic C,N‐Dianions
Author(s) -
Jeffrey Jenna L.,
Bartlett Emily S.,
Sarpong Richmond
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201209591
Subject(s) - intramolecular force , chemistry , nucleophile , product (mathematics) , combinatorial chemistry , coupling (piping) , computer science , natural product , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , mathematics , metallurgy , geometry
What a couple! An intramolecular, C(sp 3 )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 CH bonds and less reactive nitrogen nucleophiles. ZnCl 2 was identified as an important additive.