The iron-catalysed Suzuki coupling of aryl chlorides

TY - JOUR

T1 - The iron-catalysed Suzuki coupling of aryl chlorides

AU - Rowsell, Benjamin

AU - O’Brien, Harry

AU - Athavan, Gayathri

AU - Daley-Dee, Patrick

AU - Krieger, Johannes

AU - Richards, Emma

AU - Heaton, Karl

AU - Bedford, Robin

AU - Fairlamb, Ian James Stewart

N1 - © The Author(s) 2024

PY - 2024/10/17

Y1 - 2024/10/17

N2 - A simple iron-based catalyst with an N-heterocyclic carbene ligand can be used to excellent effect in the previously unknown Suzuki biaryl coupling of aryl chloride substrates with aryl boronic esters activated by an organolithium reagent. Mechanistic studies suggest the possible involvement of Fe(I) as the lowest oxidation state on the catalytic manifold and show that the challenging step is not activation of the aryl chloride substrate, but rather the transmetallation step. These findings are likely to pave the way for a renaissance of iron-catalysed carbon-carbon bond-forming transformations with ‘soft’ nucleophilic coupling partners.

AB - A simple iron-based catalyst with an N-heterocyclic carbene ligand can be used to excellent effect in the previously unknown Suzuki biaryl coupling of aryl chloride substrates with aryl boronic esters activated by an organolithium reagent. Mechanistic studies suggest the possible involvement of Fe(I) as the lowest oxidation state on the catalytic manifold and show that the challenging step is not activation of the aryl chloride substrate, but rather the transmetallation step. These findings are likely to pave the way for a renaissance of iron-catalysed carbon-carbon bond-forming transformations with ‘soft’ nucleophilic coupling partners.

U2 - 10.1038/s41929-024-01234-0

DO - 10.1038/s41929-024-01234-0

M3 - Article

SN - 2520-1158

JO - Nature Catalysis

JF - Nature Catalysis

ER -