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Elusive Metal-Free Primary Amination of Arylboronic Acids: Synthetic Studies and Mechanism by Density Functional Theory

Chen Zhu, Gongqiang Li, Daniel H. Ess, John R. Falck and László Kürti*

*Division of Chemistry, Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390, United States, Email: laszlo.kurtiutsouthwestern.edu

C. Zhu, G. Li, D. H. Ess, J. R. Falck, L. Kürti, J. Am. Chem. Soc., 2012, 134, 18253-18256.

DOI: 10.1021/ja309637r (free Supporting Information)


Abstract

A metal-free synthesis of primary aromatic amines from arylboronic acids affords structurally diverse primary arylamines in good chemical yields, including various halogenated primary anilines. The reaction is operationally simple, requires only a slight excess of aminating agent, proceeds under neutral or basic conditions, and can be scaled up to provide multigram quantities of anilines.

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Key Words

Anilines


ID: J48-Y2012-3490