Nickel or Phenanthroline Mediated Intramolecular Arylation of sp3 C–H Bonds Using Aryl Halides

The development of the intramolecular arylation of sp3 C–H bonds adjacent to nitrogen using aryl halides is described. Arylation was accomplished using either Ni(COD)2 or 1,10-phenanthroline in substoichiometric amounts, and the reaction conditions were applied to a variety of electronically differe...

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Bibliographic Details
Published in:Organic letters 2013-12, Vol.15 (23), p.5986-5989
Main Authors: Wertjes, William C, Wolfe, Lydia C, Waller, Peter J, Kalyani, Dipannita
Format: Article
Language:English
Subjects:
Benzamides - chemistry
Catalysis
Combinatorial Chemistry Techniques
Hydrocarbons, Halogenated - chemistry
Molecular Structure
Nickel - chemistry
Phenanthrolines - chemistry
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Summary:The development of the intramolecular arylation of sp3 C–H bonds adjacent to nitrogen using aryl halides is described. Arylation was accomplished using either Ni(COD)2 or 1,10-phenanthroline in substoichiometric amounts, and the reaction conditions were applied to a variety of electronically differentiated benzamide substrates. Preliminary studies suggest a mechanism involving aryl and alkyl radical intermediates.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402869h