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Transition-Metal-Free Access to Primary Anilines from Boronic Acids and a Common +NH2 Equivalent

Samantha Voth, Joshua W. Hollett and J. Adam McCubbin*

*Department of Chemistry, University of Winnipeg, 599 Portage Avenue, Winnipeg, Manitoba Canada, R3B 2E9, Email: a.mccubbinuwinnipeg.ca

S. Voth, J. W. Hollett, J. A. McCubbin, J. Org. Chem., 2015, 80, 2545-2553.

DOI: 10.1021/jo5025078 (free Supporting Information)



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Abstract

Various anilines are prepared by treatment of functionalized arylboronic acids with H2N-OSO3H (HSA) as a common, inexpensive source of electrophilic nitrogen, under basic aqueous conditions. Electron-rich substrates are found to be the most reactive by this method, whereas highly electron-deficient substrates must be converted at reflux. Sterically hindered substrates appear to be equally effective compared to unhindered ones.

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Key Words

Anilines


ID: J42-Y2015