Issue 23, 2016

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
25 Apr 2016
Accepted
11 May 2016
First published
11 May 2016
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2016,14, 5286-5292

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

C. W. Cavanagh, M. H. Aukland, Q. Laurent, A. Hennessy and D. J. Procter, Org. Biomol. Chem., 2016, 14, 5286 DOI: 10.1039/C6OB00883F

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