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

19 March 2021, Version 1

Abstract

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.

Keywords

Palladium impurities
amine catalysed Suzuki

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Version History

Mar 19, 2021 Version 1

Version Notes

Final version for submission

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.14237288.v1
D O I: 10.26434/chemrxiv.14237288.v1 [opens in a new tab]

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)).

Author’s competing interest statement

The authors declare no conflict of interest

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