Due to the synthetic advantages presented by the dual-gold-catalysed hydrophenoxylation of alkynes, a thorough study of this reaction was carried out in order to fully define the scope and limitations of the methodology. The protocol tolerates a wide range of functional groups, such as nitriles, ketones, esters, aldehydes, ketals, naphthyls, allyls or polyphenols, in a milder and more efficient manner than the previously reported methodologies. We have also identified that while we are able to use highly steric hindered phenols, small changes on the steric bulk of the alkynes have a dramatic effect on the reactivity. More importantly, we have observed that the use of substrates that facilitate the formation of diaurated species such as gem-diaurated or σ,π-digold–acetylide species, hinder the catalytic activity. Moreover, we have identified that the use of directing groups in unsymmetrical alkynes can help to achieve high regioselectivity in the hydrophenoxylation.
|Original language||English (US)|
|Number of pages||7|
|Journal||BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY|
|State||Published - Feb 1 2016|
Bibliographical noteKAUST Repository Item: Exported on 2022-05-26
Acknowledged KAUST grant number(s): OSR-2015-CCF-1974-03
Acknowledgements: The ERC (Advanced Investigator Award-FUNCAT) and Syngenta are gratefully acknowledged for support. Umicore AG is acknowledged for their generous gift of materials. This publication is based upon work supported by the King Abdullah University of Science and Technology (KAUST), Office of Sponsored Research (OSR) under Award No. OSR-2015-CCF-1974-03. Y.O. thanks the Uehara Memorial Foundation for a Research Fellowship. We also thank Danila Gasperini for early synthetic contributions and Dr. David J. Nelson for helpful discussions.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.
ASJC Scopus subject areas
- Organic Chemistry