Phenyl Hydrazine as Initiator for Direct Arene C–H Arylation via Base Promoted Homolytic Aromatic Substitution

A simple and efficient direct radical arylation of unactivated arenes is described which uses cheap and commercially available phenyl hydrazine as an initiator. The reaction occurs through a base promoted homolytic aromatic substitution (BHAS) mechanism involving aryl radicals and aryl radical anion...

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Bibliographic Details
Published in:Organic letters 2013-12, Vol.15 (23), p.6102-6105
Main Authors: Dewanji, Abhishek, Murarka, Sandip, Curran, Dennis P, Studer, Armido
Format: Article
Language:English
Subjects:
Benzene Derivatives - chemistry
Biphenyl Compounds - chemical synthesis
Biphenyl Compounds - chemistry
Catalysis
Molecular Structure
Phenylhydrazines - chemistry
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Summary:A simple and efficient direct radical arylation of unactivated arenes is described which uses cheap and commercially available phenyl hydrazine as an initiator. The reaction occurs through a base promoted homolytic aromatic substitution (BHAS) mechanism involving aryl radicals and aryl radical anions as intermediates and offers a practical approach for preparation of an array of substituted biaryls.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402995e