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dc.contributor.authorYue, Huifeng
dc.contributor.authorZhu, Chen
dc.contributor.authorKancherla, Rajesh
dc.contributor.authorLiu, Fangying
dc.contributor.authorRueping, Magnus
dc.date.accessioned2020-02-11T07:03:31Z
dc.date.available2020-02-11T07:03:31Z
dc.date.issued2020-02-03
dc.date.submitted2019-11-05
dc.identifier.citationYue, 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.doi10.1002/ange.201914061
dc.identifier.doi10.1002/anie.201914061
dc.identifier.urihttp://hdl.handle.net/10754/661463
dc.description.abstractAlkynes 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.sponsorshipC.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.publisherWiley
dc.relation.urlhttps://onlinelibrary.wiley.com/doi/abs/10.1002/ange.201914061
dc.rightsThis 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.urihttp://creativecommons.org/licenses/by-nc/4.0/
dc.titleRegioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalAngewandte Chemie
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionInstitute of Organic ChemistryRWTH Aachen University Landoltweg 1 52074 Aachen Germany
kaust.personYue, Huifeng
kaust.personZhu, Chen
kaust.personKancherla, Rajesh
kaust.personRueping, Magnus
dc.date.accepted2020-01-04
refterms.dateFOA2020-02-11T07:05:33Z
kaust.acknowledged.supportUnitsupercomputer Shaheen II
kaust.acknowledged.supportUnitSupercomputing Laboratory
dc.date.published-online2020-02-03
dc.date.published-print2020-03-27


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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.
Except where otherwise noted, this item's license is described as 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.