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

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0008-9B8B-D Version Permalink: https://hdl.handle.net/21.11116/0000-0008-9B8C-C
Genre: Journal Article

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 Creators:
Cavanagh, Craig W.1, Author
Aukland, Miles H.1, Author           
Laurent, Quentin1, Author
Hennessy, Alan2, Author
Procter, David J.1, Author
Affiliations:
1Department of Chemistry, University of Manchester, Manchester, UK, ou_persistent22              
2Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire, UK , ou_persistent22              

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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.

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Language(s): eng - English
 Dates: 2016-04-252016-05-112016-06-21
 Publication Status: Issued
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1039/C6OB00883F
 Degree: -

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Title: Organic & Biomolecular Chemistry
  Other : Organic and Biomolecular Chemistry
  Abbreviation : Org. Biomol. Chem.
Source Genre: Journal
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Publ. Info: Cambridge : Royal Society of Chemistry
Pages: - Volume / Issue: 14 (23) Sequence Number: - Start / End Page: 5286 - 5292 Identifier: ISSN: 1477-0520
CoNE: https://pure.mpg.de/cone/journals/resource/954925269322