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Ring-expanded N-heterocyclic carbenes as ligands in iron-catalysed cross-coupling reactions of arylmagnesium reagents and aryl chlorides

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Abstract

The structure–activity relationship of expanded-ring N-heterocyclic carbenes (NHCs) in the iron-catalysed Kumada aryl–aryl coupling reaction was explored. This was achieved by comparing the catalytic performance of Fe-NHC catalysts generated in situ containing NHCs that differ in steric bulk. In particular, the influences of ring sizes (5–8) and N-aryl substituents were explored in terms of spectroscopic and structural features, which affect their %Vbur values. The three best performing ligands were found on a diagonal of a 5 × 4 structural matrix revealing an optimal steric bulk and significant influences of subtle steric variations on the catalytic activities.

Graphical abstract: Ring-expanded N-heterocyclic carbenes as ligands in iron-catalysed cross-coupling reactions of arylmagnesium reagents and aryl chlorides

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Publication details

The article was received on 06 Mar 2018, accepted on 16 May 2018 and first published on 17 May 2018


Article type: Communication
DOI: 10.1039/C8CC01808A
Citation: Chem. Commun., 2018, Advance Article
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    Ring-expanded N-heterocyclic carbenes as ligands in iron-catalysed cross-coupling reactions of arylmagnesium reagents and aryl chlorides

    Q. Teng, W. Wu, H. A. Duong and H. V. Huynh, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC01808A

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