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

Veenboer, Richard M. P.; Nolan, Steven P.

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

Type

Article

Authors

Veenboer, Richard M. P.

Nolan, Steven P.

Date

2015

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.

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.