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

Craig Cavanagh; Miles Aukland; Quentin Laurent; Alan Hennessy; David Procter

doi:10.1039/c6ob00883f

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

Craig Cavanagh, Miles Aukland, Quentin Laurent, Alan Hennessy, David Procter^*

^*Corresponding author for this work

Syngenta UK

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	5286-5292
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	23
Early online date	11 May 2016
DOIs	https://doi.org/10.1039/c6ob00883f
Publication status	Published - 21 Jun 2016

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10.1039/c6ob00883fLicence: CC BY

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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.",

author = "Craig Cavanagh and Miles Aukland and Quentin Laurent and Alan Hennessy and David Procter",

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AU - Cavanagh, Craig

AU - Aukland, Miles

AU - Laurent, Quentin

AU - Hennessy, Alan

AU - Procter, David

PY - 2016/6/21

Y1 - 2016/6/21

N2 - 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.

AB - 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.

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DO - 10.1039/c6ob00883f

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 23

ER -

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

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