Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 38, Pages 12771-12777Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201301800
Keywords
amination; copper; enamides; indoles; oxidation
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Funding
- National Institutes of Health, NIGMS [GM-078383]
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Enamines and enamides are useful synthetic intermediates and common components of bioactive compounds. A new protocol for their direct synthesis by a net alkene CH amination and allylic amination by using catalytic Cu-II in the presence of MnO2 is reported. Reactions between N-aryl sulfonamides and vinyl arenes furnish enamides, allylic amines, indoles, benzothiazine dioxides, and dibenzazepines directly and efficiently. Control experiments further showed that MnO2 alone can promote the reaction in the absence of a copper salt, albeit with lower efficiency. Mechanistic probes support the involvement of nitrogen-radical intermediates. This method is ideal for the synthesis of enamides from 1,1-disubstituted vinyl arenes, which are uncommon substrates in existing oxidative amination protocols.
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