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Issue 23, 2016
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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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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

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Supplementary files

Article information


Submitted
25 Apr 2016
Accepted
11 May 2016
First published
11 May 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 5286-5292
Article type
Paper

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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