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

Richard M. P. Veenboer; Steven P. Nolan

doi:10.1039/c5gc00684h

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

Richard M. P. Veenboer, Steven P. Nolan

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

25 Scopus citations

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.

Original language	English (US)
Pages (from-to)	3819-3825
Number of pages	7
Journal	Green Chem.
Volume	17
Issue number	7
DOIs	https://doi.org/10.1039/c5gc00684h
State	Published - 2015
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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title = "Gold( i )-catalysed dehydrative formation of ethers from benzylic alcohols and phenols",

abstract = "{\textcopyright} 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.",

author = "Veenboer, {Richard M. P.} and Nolan, {Steven P.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

year = "2015",

doi = "10.1039/c5gc00684h",

language = "English (US)",

volume = "17",

pages = "3819--3825",

journal = "Green Chem.",

issn = "1463-9262",

publisher = "Royal Society of Chemistry",

number = "7",

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T1 - Gold( i )-catalysed dehydrative formation of ethers from benzylic alcohols and phenols

AU - Veenboer, Richard M. P.

AU - Nolan, Steven P.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2015

Y1 - 2015

N2 - © 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.

AB - © 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.

UR - http://hdl.handle.net/10754/598422

UR - http://xlink.rsc.org/?DOI=C5GC00684H

UR - http://www.scopus.com/inward/record.url?scp=84936792264&partnerID=8YFLogxK

U2 - 10.1039/c5gc00684h

DO - 10.1039/c5gc00684h

M3 - Article

SN - 1463-9262

VL - 17

SP - 3819

EP - 3825

JO - Green Chem.

JF - Green Chem.

IS - 7

ER -

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

Abstract

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