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Amine-Catalysed Suzuki–Miyaura-Type Coupling? the Identification and Isolation of the Palladium Culprits.
preprintsubmitted on 18.03.2021, 14:19 and posted on 19.03.2021, 13:36 by Mickaël Avanthay, Robin Bedford, Callum Begg, Dietrich Böse, Jonathan Clayden, Sean Davis, Jean-Charles Eloi, Georgy P. Goryunov, Ingo V. Hartung, Joseph Heeley, Kirill A. Khaikin, Matthew Kitching, Johannes Krieger, Pavel S. Kulyabin, Alastair Lennox, Roberto Nolla-Saltiel, Natalie E. Pridmore, Benjamin J. S. Rowsell, Hazel A. Sparkes, Dmitry V. Uborsky, Alexander Z. Voskoboynikov, Mark Walsh, Harry J. Wilkinson
A recent report in Nature Catalysis detailed the potentially paradigm-shifting organocatalysis of Suzuki cross-coupling of aryl halides with aryl boronic acids, catalysed by simple amine species. We have conducted a reinvestigation of key claims in this paper across multiple academic and industrial laboratories that shows that the observed catalytic activity cannot be due to the amine, but rather is due to tricyclohexylphosphine palladium complexes that are readily entrained during the purification of the amine.