Synfacts 2020; 16(04): 0409
DOI: 10.1055/s-0040-1707562
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Bismuth Redox-Catalyzed Fluorination of Arylboron Reagents

Paul Knochel
Simon Graßl
Planas O, Wang F, Leutzsch M, Cornella J. * Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Fluorination of Arylboronic Esters Enabled by Bismuth Redox Catalysis.

Science 2020;
367: 313-317
Further Information

Publication History

Publication Date:
18 March 2020 (online)



The authors report a bismuth ­redox-catalyzed fluorination of functionalized arylboronic esters or acids. The key role is played by the newly designed bismuth complex, which can change oxidation state and therefore undergo both oxidative addition and reductive elimination like a transition metal.



Based on crystallographic characterization of the bismuth species involved, combined with mechanistic investigations, Cornella and co-workers revealed the presence of a Bi(III)/Bi(V) redox couple, which has never been observed before. This work demonstrates the possibility of giving non-d-block elements transition-metal-like behavior by careful tuning of the ligand.