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

Richard MP Veenboer and Steven Nolan (UGent)
(2015) GREEN CHEMISTRY. 17(7). p.3819-3825
Author
Organization
Abstract
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.
Keywords
PROPARGYLIC SUBSTITUTION-REACTIONS, C-H ALKYLATION, NUCLEOPHILIC-SUBSTITUTION, UNSYMMETRICAL ETHERS, BRONSTED ACID, ORGANIC TRANSFORMATIONS, EFFICIENT CATALYST, SODIUM BISULFITE, GOLD CATALYSIS, BOND FORMATION

Citation

Please use this url to cite or link to this publication:

MLA
Veenboer, Richard MP, and Steven Nolan. “Gold(I)-Catalysed Dehydrative Formation of Ethers from Benzylic Alcohols and Phenols.” GREEN CHEMISTRY, vol. 17, no. 7, 2015, pp. 3819–25.
APA
Veenboer, R. M., & Nolan, S. (2015). Gold(I)-catalysed dehydrative formation of ethers from benzylic alcohols and phenols. GREEN CHEMISTRY, 17(7), 3819–3825.
Chicago author-date
Veenboer, Richard MP, and Steven Nolan. 2015. “Gold(I)-Catalysed Dehydrative Formation of Ethers from Benzylic Alcohols and Phenols.” GREEN CHEMISTRY 17 (7): 3819–25.
Chicago author-date (all authors)
Veenboer, Richard MP, and Steven Nolan. 2015. “Gold(I)-Catalysed Dehydrative Formation of Ethers from Benzylic Alcohols and Phenols.” GREEN CHEMISTRY 17 (7): 3819–3825.
Vancouver
1.
Veenboer RM, Nolan S. Gold(I)-catalysed dehydrative formation of ethers from benzylic alcohols and phenols. GREEN CHEMISTRY. 2015;17(7):3819–25.
IEEE
[1]
R. M. Veenboer and S. Nolan, “Gold(I)-catalysed dehydrative formation of ethers from benzylic alcohols and phenols,” GREEN CHEMISTRY, vol. 17, no. 7, pp. 3819–3825, 2015.
@article{8168385,
  abstract     = {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 MP and Nolan, Steven},
  issn         = {1463-9262},
  journal      = {GREEN CHEMISTRY},
  keywords     = {PROPARGYLIC SUBSTITUTION-REACTIONS,C-H ALKYLATION,NUCLEOPHILIC-SUBSTITUTION,UNSYMMETRICAL ETHERS,BRONSTED ACID,ORGANIC TRANSFORMATIONS,EFFICIENT CATALYST,SODIUM BISULFITE,GOLD CATALYSIS,BOND FORMATION},
  language     = {eng},
  number       = {7},
  pages        = {3819--3825},
  title        = {Gold(I)-catalysed dehydrative formation of ethers from benzylic alcohols and phenols},
  url          = {http://dx.doi.org/10.1039/c5gc00684h},
  volume       = {17},
  year         = {2015},
}
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