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. 2013 Dec 6;15(23):6102-5.
doi: 10.1021/ol402995e. Epub 2013 Nov 19.

Phenyl hydrazine as initiator for direct arene C-H arylation via base promoted homolytic aromatic substitution

Abhishek Dewanji  1 , Sandip Murarka, Dennis P Curran, Armido Studer
Affiliations

Phenyl hydrazine as initiator for direct arene C-H arylation via base promoted homolytic aromatic substitution

Abhishek Dewanji et al. Org Lett. .

Abstract

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.

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Figures

Scheme 1
Scheme 1
Base Promoted Biaryl Synthesis via Homolytic Aromatic Substitution
Scheme 2
Scheme 2
Terphenyl Synthesis via Direct Bisarylation of Haloiodoarenes
Scheme 3
Scheme 3
Proposed Mechanism
See this image and copyright information in PMC

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