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Asymmetric azide‐alkyne Huisgen cycloaddition on chiral metal surfaces

Samuel Stolz1,2*, Michael Bauer3, Carlo A. Pignedoli1*, Nils Krane1, Max Bommert1, Elia Turco1, Nicolo Bassi1, Amogh Kinikar1, Néstor Merino-Dìez1, Roland Hany3, Harald Brune2, Oliver Gröning1, Roland Widmer1*

1 Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 Dübendorf, Switzerland

2 Institute of Physics, École Polytechnique Fédérale de Lausanne, Laboratory of Nanostructures at Surfaces, 1015 Lausanne, Switzerland

3 Empa, Swiss Federal Laboratories for Materials Science and Technology, Laboratory for Functional Polymers, 8600 Dübendorf, Switzerland

* Corresponding authors emails: samuel.stolz@empa.ch, carlo.pignedoli@empa.ch, roland.widmer@empa.ch
DOI10.24435/materialscloud:tx-8g [version v1]

Publication date: Mar 02, 2021

How to cite this record

Samuel Stolz, Michael Bauer, Carlo A. Pignedoli, Nils Krane, Max Bommert, Elia Turco, Nicolo Bassi, Amogh Kinikar, Néstor Merino-Dìez, Roland Hany, Harald Brune, Oliver Gröning, Roland Widmer, Asymmetric azide‐alkyne Huisgen cycloaddition on chiral metal surfaces, Materials Cloud Archive 2021.38 (2021), doi: 10.24435/materialscloud:tx-8g.

Description

The record contains the data supporting our recent findings on asymmetric azide-alkyne Huisgen cycloaddition on chiral metal surfaces: Achieving fundamental understanding of enantioselective heterogeneous synthesis is marred by the permanent presence of multitudinous arrangements of catalytically active sites in real catalysts. We address this issue by using structurally comparatively simple, well‐defined, and chiral intermetallic PdGa{111} surfaces as catalytic substrates. We demonstrate the impact of chirality transfer and ensemble effect for the thermally activated azide‐alkyne Huisgen cycloaddition between 3‐(4‐azidophenyl)propionic acid and 9‐ethynylphenanthrene on these threefold symmetric intermetallic surfaces under ultrahigh vacuum conditions. Specifically, we encounter a dominating ensemble effect for this reaction as on the Pd3‐terminated PdGa{111} surfaces no stable heterocoupled structures are created, while on the Pd1‐terminated PdGa{111} surfaces, the cycloaddition proceeds regioselectively. Moreover, we observe chirality transfer from the substrate to the reaction products, as they are formed enantioselectively on the Pd1‐terminated PdGa{111} surfaces. Our results evidence a determinant ensemble effect and the immense potential of PdGa as asymmetric heterogeneous catalyst.

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Files and data are licensed under the terms of the following license: Creative Commons Attribution 4.0 International.
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External references

Journal reference (Manuscript where the results are discussed.)
S. Stolz, M. Bauer, C. A. Pignedoli, N. Krane, M. Bommert, E. Turco, N. Bassi, A. Kinikar, N. Merino-Dìez, R. Hany, H. Brune, O. Gröning, R. Widmer, Commun. Chem., in press (2021)

Keywords

SNSF Azide‐alkyne Huisgen cycloaddition asymmetric heterogeneous catalysis on‐surface synthesis ab-initio simulations Experimental

Version history:

2021.38 (version v1) [This version] Mar 02, 2021 DOI10.24435/materialscloud:tx-8g