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

Richard Marinus Petrus Veenboer; Steven Patrick Nolan

doi:10.1039/C5GC00684H

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

Richard Marinus Petrus Veenboer, Steven Patrick Nolan

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

Abstract

We report the cross-dehydrative reaction of two alcohols to form unsymmetrical ethers using NHC-gold(I) complexes (NHC = N-heterocylic carbene). 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 forming a range of ethers from readily available phenols bearing electron-withdrawing substituents and secondary benzylic alcohols with various substituents. Finally, the chemoselectivity obtained in these reactions is explained.

Original language	English
Pages (from-to)	3819-3825
Number of pages	8
Journal	Green Chemistry
Volume	17
Issue number	7
Early online date	8 May 2015
DOIs	https://doi.org/10.1039/C5GC00684H
Publication status	Published - 1 Jul 2015

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10.1039/C5GC00684H

Nolan_2015_GC_Gold_CC
Copyright 2015 the Authors. This open access article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
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title = "Gold(I)-catalysed dehydrative formation of ethers from benzylic alcohols and phenols",

abstract = "We report the cross-dehydrative reaction of two alcohols to form unsymmetrical ethers using NHC-gold(I) complexes (NHC = N-heterocylic carbene). 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 forming a range of ethers from readily available phenols bearing electron-withdrawing substituents and secondary benzylic alcohols with various substituents. Finally, the chemoselectivity obtained in these reactions is explained.",

author = "Veenboer, {Richard Marinus Petrus} and Nolan, {Steven Patrick}",

note = "The EPSRC and ERC are gratefully acknowledged for support. S.P.N. is a Royal Society Wolfson Research Merit Award holder. ",

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AU - Veenboer, Richard Marinus Petrus

AU - Nolan, Steven Patrick

N1 - The EPSRC and ERC are gratefully acknowledged for support. S.P.N. is a Royal Society Wolfson Research Merit Award holder.

PY - 2015/7/1

Y1 - 2015/7/1

N2 - We report the cross-dehydrative reaction of two alcohols to form unsymmetrical ethers using NHC-gold(I) complexes (NHC = N-heterocylic carbene). 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 forming a range of ethers from readily available phenols bearing electron-withdrawing substituents and secondary benzylic alcohols with various substituents. Finally, the chemoselectivity obtained in these reactions is explained.

AB - We report the cross-dehydrative reaction of two alcohols to form unsymmetrical ethers using NHC-gold(I) complexes (NHC = N-heterocylic carbene). 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 forming a range of ethers from readily available phenols bearing electron-withdrawing substituents and secondary benzylic alcohols with various substituents. Finally, the chemoselectivity obtained in these reactions is explained.

UR - http://www.rsc.org/suppdata/c5/gc/c5gc00684h/c5gc00684h1.pdf

U2 - 10.1039/C5GC00684H

DO - 10.1039/C5GC00684H

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SP - 3819

EP - 3825

JO - Green Chemistry

JF - Green Chemistry

IS - 7

ER -

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

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EPSRC - EP/J011053/1- LATE TRANSITION: Late Transition Metal Hydroxide in Homogeneous Catalysis

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

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EPSRC - EP/J011053/1- LATE TRANSITION: Late Transition Metal Hydroxide in Homogeneous Catalysis

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