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)
see article for more reactions
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.
see article for more examples