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Iron-catalyzed C(sp2)–C(sp3) cross-coupling at low catalyst loading

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Abstract

The iron-catalyzed C(sp2)–C(sp3) cross-coupling provides a highly economical route to exceedingly valuable alkylated arenes that are widespread in medicinal chemistry and materials science. Herein, we report an operationally-simple protocol for the selective C(sp2)–C(sp3) iron-catalyzed cross-coupling of aryl chlorides with Grignard reagents at low catalyst loading. A broad range of electronically-varied aryl and heteroaryl chlorides underwent the cross-coupling using challenging alkyl organometallics possessing β-hydrogens with high efficiency up to 2000 TON. A notable feature of the protocol is the use of environmentally-friendly cyclic urea ligands. A series of guidelines to predict cross-coupling reactivity of aryl electrophiles is provided.

Graphical abstract: Iron-catalyzed C(sp2)–C(sp3) cross-coupling at low catalyst loading

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Publication details

The article was received on 21 Nov 2018, accepted on 04 Feb 2019 and first published on 05 Feb 2019


Article type: Communication
DOI: 10.1039/C8CY02374C
Citation: Catal. Sci. Technol., 2019, Advance Article

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    Iron-catalyzed C(sp2)–C(sp3) cross-coupling at low catalyst loading

    E. Bisz, M. Kardela, A. Piontek and M. Szostak, Catal. Sci. Technol., 2019, Advance Article , DOI: 10.1039/C8CY02374C

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