Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C-N Bond Activation
Prantik Maity, Danielle M. Shacklady-McAtee, Glenn P. A. Yap, Eric R. Sirianni and Mary P. Watson*
*Department of Chemistry and Biochemistry, University of
Delaware, Newark, Delaware 19716, United States, Email: mpwatson
udel.edu
P. Maity, D. M. Shacklady-McAtee, G. P. A. Yap, E. R. Sirianni, M. P. Watson, J. Am. Chem. Soc., 2013, 135, 280-285.
DOI: 10.1021/ja3089422
Abstract
A nickel-catalyzed cross coupling of benzylic ammonium triflates with aryl boronic acids affords diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts with excellent chirality transfer, offering a new strategy for the synthesis of highly enantioenriched diarylethanes.
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ID: J48-Y2013-0030
