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

Abhishek Dewanji, Sandip Murarka, Dennis P. Curran* and Armido Studer*

*Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149 Münster, Germany; University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States, Email: studeruni-muenster.de, curranpitt.edu

A. Dewanji, S. Murarka, D. P. Curran, A. Studer, Org. Lett., 2013, 15, 6102-6105.

DOI: 10.1021/ol402995e

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Abstract

In a simple and efficient direct radical arylation of unactivated arenes, cheap and commercially available phenyl hydrazine is used as an initiator. The reaction occurs through a base promoted homolytic aromatic substitution (BHAS) mechanism via 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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Key Words

Biaryls

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ID: J54-Y2013