Gold( i )-catalysed dehydrative formation of ethers from benzylic alcohols and phenols
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ArticleDate
2015Permanent link to this record
http://hdl.handle.net/10754/598422
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© 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.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.Publisher
Royal Society of Chemistry (RSC)Journal
Green Chemistryae974a485f413a2113503eed53cd6c53
10.1039/c5gc00684h