Iron-mediated oxidative C–H coupling of arenes and alkenes directed by sulfur: 
an expedient route to dihydrobenzofurans

Cavanagh, Craig W.; Aukland, Miles H.; Laurent, Quentin; Hennessy, Alan; Procter, David J.

doi:10.1039/C6OB00883F

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Iron-mediated oxidative C–H coupling of arenes and alkenes directed by sulfur: an expedient route to dihydrobenzofurans

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Cavanagh, C. W., Aukland, M. H., Laurent, Q., Hennessy, A., & Procter, D. J. (2016). Iron-mediated oxidative C–H coupling of arenes and alkenes directed by sulfur: an expedient route to dihydrobenzofurans. Organic & Biomolecular Chemistry, 14(23), 5286-5292. doi:10.1039/C6OB00883F.

Cite as: https://hdl.handle.net/21.11116/0000-0008-9B8B-D

Abstract

A novel route to medicinally-relevant dihydrobenzofurans utilises a sulfur-directed C–H ortho-coupling of arenes and unactivated terminal alkenes mediated by iron, and a palladium-catalysed deallylation/heterocyclisation sequence. The iron-mediated coupling affords linear products of alkene chloroarylation in good yield and with complete regioselectivity. The coupling likely proceeds by redox-activation of the arene partner by iron(III) and alkene addition to the resultant radical cation.