Gold( i )-catalysed dehydrative formation of ethers from benzylic alcohols and phenols

Handle URI:
http://hdl.handle.net/10754/598422
Title:
Gold( i )-catalysed dehydrative formation of ethers from benzylic alcohols and phenols
Authors:
Veenboer, Richard M. P.; Nolan, Steven P.
Abstract:
© The Royal Society of Chemistry 2015. We report the cross-dehydrative reaction of two alcohols to form unsymmetrical ethers using NHC-gold(i) complexes (NHC = N-heterocyclic carbene). Our progress in developing this reaction into a straightforward procedure is discussed in detail. The optimised methodology proceeds under mild reaction conditions and produces water as the sole by-product. The synthetic utility of this environmentally benign methodology is exemplified by the formation of a range of new ethers from readily available phenols bearing electron withdrawing substituents and secondary benzylic alcohols with various substituents. Finally, we present experimental results to account for the chemoselectivity obtained in these reactions.
Citation:
Veenboer RMP, Nolan SP (2015) Gold( i )-catalysed dehydrative formation of ethers from benzylic alcohols and phenols . Green Chem 17: 3819–3825. Available: http://dx.doi.org/10.1039/c5gc00684h.
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Green Chem.
Issue Date:
2015
DOI:
10.1039/c5gc00684h
Type:
Article
ISSN:
1463-9262; 1463-9270
Sponsors:
The EPSRC and ERC are gratefully acknowledged for support. KAUST is gratefully acknowledged for partial support of this work. Umicore AG is acknowledged for their generous gift of materials. The EPSRC National Mass Spectrometry Service Centre (NMSSC) is gratefully acknowledged for HRMS analyses. S.P.N. is a Royal Society Wolfson Research Merit Award holder.
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Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorVeenboer, Richard M. P.en
dc.contributor.authorNolan, Steven P.en
dc.date.accessioned2016-02-25T13:20:27Zen
dc.date.available2016-02-25T13:20:27Zen
dc.date.issued2015en
dc.identifier.citationVeenboer RMP, Nolan SP (2015) Gold( i )-catalysed dehydrative formation of ethers from benzylic alcohols and phenols . Green Chem 17: 3819–3825. Available: http://dx.doi.org/10.1039/c5gc00684h.en
dc.identifier.issn1463-9262en
dc.identifier.issn1463-9270en
dc.identifier.doi10.1039/c5gc00684hen
dc.identifier.urihttp://hdl.handle.net/10754/598422en
dc.description.abstract© The Royal Society of Chemistry 2015. We report the cross-dehydrative reaction of two alcohols to form unsymmetrical ethers using NHC-gold(i) complexes (NHC = N-heterocyclic carbene). Our progress in developing this reaction into a straightforward procedure is discussed in detail. The optimised methodology proceeds under mild reaction conditions and produces water as the sole by-product. The synthetic utility of this environmentally benign methodology is exemplified by the formation of a range of new ethers from readily available phenols bearing electron withdrawing substituents and secondary benzylic alcohols with various substituents. Finally, we present experimental results to account for the chemoselectivity obtained in these reactions.en
dc.description.sponsorshipThe EPSRC and ERC are gratefully acknowledged for support. KAUST is gratefully acknowledged for partial support of this work. Umicore AG is acknowledged for their generous gift of materials. The EPSRC National Mass Spectrometry Service Centre (NMSSC) is gratefully acknowledged for HRMS analyses. S.P.N. is a Royal Society Wolfson Research Merit Award holder.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleGold( i )-catalysed dehydrative formation of ethers from benzylic alcohols and phenolsen
dc.typeArticleen
dc.identifier.journalGreen Chem.en
dc.contributor.institutionUniversity of St Andrews, St. Andrews, United Kingdomen
dc.contributor.institutionKing Saud University College of Science, Riyadh, Saudi Arabiaen
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