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Amine-catalysed Suzuki–Miyaura-type coupling. The identification and isolation of the palladium culprits..pdf (2.86 MB)

Amine-Catalysed Suzuki–Miyaura-Type Coupling? the Identification and Isolation of the Palladium Culprits.

preprint
submitted 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.

Funding

We thank the Chemical Synthesis Centre for Doctoral Training (funded by EPSRC (EP/L015366/1), AstraZeneca, GlaxoSmithKline, Syngenta, UCB, Ziylo and the University of Bristol) for the provision of a PhD studentship (BJSR); the Technology Enhanced Chemical Synthesis Centre for Doctoral Training (funded by EPSRC (EP/S024107/1), AstraZeneca, Astex, Bayer, GlaxoSmithKline, Syngenta, Vertex and the University of Bristol) for the provision of an PhD studentship (JH); GSK (iCASE studentship to MA); the EPSRC (PhD studentship to CSB, EP/T518001/1, project reference 2456710); the UK Catalysis Hub (support provided to RBB, AJJL and RN-S for our membership of the UK Catalysis Hub Consortium, funded by EPSRC grant EP/R027129/1, EP/S018050/1)); the ERC (Advanced Grant 883786 to JC) and the Royal Society (University Research Fellowship to AJJL; Research Fellowship to MOK (UF150536) and equipment grant (RGS\R2\180467)).

History

Email Address of Submitting Author

r.bedford@bristol.ac.uk

Institution

University of Bristol

Country

UK

ORCID For Submitting Author

0000-0002-8021-8768

Declaration of Conflict of Interest

The authors declare no conflict of interest

Version Notes

Final version for submission

Exports

ChemRxiv

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