Iron-catalysed substrate-directed Suzuki biaryl cross-coupling

O'Brien, Harry; Manzotti, Michela; Abrams, Roman; Elorriaga, David; Sparkes, Hazel A.; Davis, Sean A.; Bedford, Robin B.

doi:10.1038/s41929-018-0081-x

Cited by 80 publications

(50 citation statements)

References 59 publications

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“…A radical mechanism was proposed due to inhibition of the coupling process in the presence of radical scavenger (TEMPO, Table 1, entry 26). 105 Interestingly, this result would suggest radical activation of the aryl─Cl bond and subsequent formation of Csp2-centred radicals, as reported for related cobalt-catalysed systems. 112 iv) Other systems Fürstner and co-workers reported the reactivity of low-valent iron(-II) ferrate ([Fe -II (η 2 -C2H4)4][Li(tmeda)]2) in aryl-alkyl crosscouplings (Table 1, Entry 27).…”

Section: Ii) Systems Involving N-ligandssupporting

confidence: 55%

Iron and cobalt catalysis: new perspectives in synthetic radical chemistry

et al. 2020

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Section: Ii) Systems Involving N-ligandssupporting

confidence: 55%

Iron and cobalt catalysis: new perspectives in synthetic radical chemistry

et al. 2020

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“…The activity of iron catalysts in diverse cross-coupling reactions can be controlled via the ligands, for example bis(imino)pyridine 8) or N-heterocyclic carbenes 9) .…”

Section: Ligands In Cross-couplingsmentioning

confidence: 99%

Some trends in sustainable catalysis development

Galstyan¹

2021

Nachr Chem

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“…Palladium catalysts have traditionally been ubiquitous in cross-coupling reactions. Utilizing iron for the Suzuki coupling to provide simple biaryl compounds remained elusive until recently, when the group of Bedford showed that simple π-coordinating N-pyrrole amides on the aryl halide substrate could facilitate activation of the relatively unreactive C-X bond (Scheme 18) [48]. The use of an NHC ligand with the appropriate steric bulk proved crucial.…”

Section: Cross-coupling Reactionsmentioning

confidence: 99%

On the Use of Iron in Organic Chemistry

Guðmundsson

Bäckvall

2020

Molecules

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Transition metal catalysis in modern organic synthesis has largely focused on noble transition metals like palladium, platinum and ruthenium. The toxicity and low abundance of these metals, however, has led to a rising focus on the development of the more sustainable base metals like iron, copper and nickel for use in catalysis. Iron is a particularly good candidate for this purpose due to its abundance, wide redox potential range, and the ease with which its properties can be tuned through the exploitation of its multiple oxidation states, electron spin states and redox potential. This is a fact made clear by all life on Earth, where iron is used as a cornerstone in the chemistry of living processes. In this mini review, we report on the general advancements in the field of iron catalysis in organic chemistry covering addition reactions, C-H activation, cross-coupling reactions, cycloadditions, isomerization and redox reactions.

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Iron-catalysed substrate-directed Suzuki biaryl cross-coupling

Abstract: Iron-catalysed substrate-directed Suzuki biaryl cross-coupling.

Cited by 80 publications

References 59 publications

Iron and cobalt catalysis: new perspectives in synthetic radical chemistry

Iron and cobalt catalysis: new perspectives in synthetic radical chemistry

Some trends in sustainable catalysis development

On the Use of Iron in Organic Chemistry

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