Journal
JOURNAL OF CATALYSIS
Volume 391, Issue -, Pages 48-55Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.jcat.2020.07.029
Keywords
Alkoxyarylation; Alkynes; Catalysis photoredox; Counterion influence; Gold; Homogeneous catalysis
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Funding
- AEI (MICIU)
- FEDER [PGC2018-095025-B-I00]
- Ministerio de Ciencia, Innovacion y Universidades [CTQ2016-75023-C2-2-P]
- Xunta de Galicia [EDC431C-2017/70]
- CITACA Strategic Partnership (Xunta de Galicia, Spain) [ED431E 2018/07]
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Since earlier work on the use of arenediazonium tetrafluoroborates under gold-photoredox co-catalyzed activation of alkynes has been developed using Ar3PAuCl salts, we focused on modifying the gold precatalyst. The use of the gold complex [Ph3PAuNTf2] allowed for a direct alkoxyarylation of alkynes to form enol ethers in a stereoselective manner, instead of the previously obtained ketones. The synthetic utility of these enol ethers was demonstrated with the controlled preparation of deuterated ketones and fluorinated ketals. Additionally, the mechanism of this alkoxyarylation variant has been explored with density functional theory (DFT) calculations. (C) 2020 Elsevier Inc. All rights reserved.
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