Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism
dc.contributor.author | Yue, Huifeng | |
dc.contributor.author | Zhu, Chen | |
dc.contributor.author | Kancherla, Rajesh | |
dc.contributor.author | Liu, Fangying | |
dc.contributor.author | Rueping, Magnus | |
dc.date.accessioned | 2020-02-11T07:03:31Z | |
dc.date.available | 2020-02-11T07:03:31Z | |
dc.date.issued | 2020-02-03 | |
dc.date.submitted | 2019-11-05 | |
dc.identifier.citation | Yue, H., Zhu, C., Kancherla, R., Liu, F., & Rueping, M. (2020). Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism. Angewandte Chemie. doi:10.1002/ange.201914061 | |
dc.identifier.doi | 10.1002/ange.201914061 | |
dc.identifier.doi | 10.1002/anie.201914061 | |
dc.identifier.uri | http://hdl.handle.net/10754/661463 | |
dc.description.abstract | Alkynes are an important class of organic molecules due to their utility as versatile building blocks in synthesis. Although efforts have been devoted to the difunctionalization of alkynes, general and practical strategies for the direct hydroalkylation and alkylarylation of terminal alkynes under mild reaction conditions are less explored. Herein, we report a photoredox/nickel dual-catalyzed anti-Markovnikov-type hydroalkylation of terminal alkynes as well as a one-pot arylalkylation of alkynes with alkyl carboxylic acids and aryl bromides via a three-component cross-coupling. The results indicate that the transformations proceed via a new mechanism involving a single-electron transfer with subsequent energy-transfer activation pathways. Moreover, steady-state and time-resolved fluorescence-spectroscopy measurements, density functional theory (DFT) calculations, and wavefunction analysis have been performed to give an insight into the catalytic cycle. | |
dc.description.sponsorship | C.Z. acknowledges the King Abdullah University of Scienceand Technology (KAUST) for support and the KAUSTSupercomputing Laboratory for providing computationalresources of the supercomputer Shaheen II. The researchleading to these results has received funding from the European Research Council under the European Union sSeventh Framework Programme (FP/2007–2013)/ERC Grant Agreement no. 617044 (SunCatChem). | |
dc.publisher | Wiley | |
dc.relation.url | https://onlinelibrary.wiley.com/doi/abs/10.1002/ange.201914061 | |
dc.rights | This is an open access article under the terms of the Creative Commons Attribution-NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. | |
dc.rights.uri | http://creativecommons.org/licenses/by-nc/4.0/ | |
dc.title | Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism | |
dc.type | Article | |
dc.contributor.department | Chemical Science Program | |
dc.contributor.department | KAUST Catalysis Center (KCC) | |
dc.contributor.department | Physical Science and Engineering (PSE) Division | |
dc.identifier.journal | Angewandte Chemie | |
dc.eprint.version | Publisher's Version/PDF | |
dc.contributor.institution | Institute of Organic ChemistryRWTH Aachen University Landoltweg 1 52074 Aachen Germany | |
kaust.person | Yue, Huifeng | |
kaust.person | Zhu, Chen | |
kaust.person | Kancherla, Rajesh | |
kaust.person | Rueping, Magnus | |
dc.date.accepted | 2020-01-04 | |
refterms.dateFOA | 2020-02-11T07:05:33Z | |
kaust.acknowledged.supportUnit | supercomputer Shaheen II | |
kaust.acknowledged.supportUnit | Supercomputing Laboratory | |
dc.date.published-online | 2020-02-03 | |
dc.date.published-print | 2020-03-27 |
Files in this item
This item appears in the following Collection(s)
-
Articles
-
Physical Science and Engineering (PSE) Division
For more information visit: http://pse.kaust.edu.sa/ -
Chemical Science Program
For more information visit: https://pse.kaust.edu.sa/study/academic-programs/chemical-science/Pages/home.aspx -
KAUST Catalysis Center (KCC)