(Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst
We communicate a versatile and user-friendly Cu-based catalytic method that allows for the selective hydrogenation of enoates and alkynes. The introduced protocol is free from any ex ante modifications of the used Cu(I) precursors by air-sensitive phosphines or elaborate N-heterocyclic carbene ligan...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-12-01
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| Series: | Tetrahedron Chem |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666951X24000287 |
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| author | Samuel Redl Christoph Topf |
| author_facet | Samuel Redl Christoph Topf |
| author_sort | Samuel Redl |
| collection | DOAJ |
| description | We communicate a versatile and user-friendly Cu-based catalytic method that allows for the selective hydrogenation of enoates and alkynes. The introduced protocol is free from any ex ante modifications of the used Cu(I) precursors by air-sensitive phosphines or elaborate N-heterocyclic carbene ligands. The conjugate hydrogenation of enoates and the (selective) reduction of C≡C bonds is achieved through a [Cu(CH3CN)4]+/tert-butoxide pair whereby we describe a delicate influence of the base cation on the chemoselectivity of the respective transformation. In case of the ester-to-alcohol reduction, a combination of simple CuI and NaOtBu proved to be successful. Deuteration experiments are included to address certain mechanistic aspects of the introduced catalytic system. All requisite chemicals are readily obtainable through commercial channels and the catalyst assembly is set up on the bench without the need for special lab-technical precautions. |
| format | Article |
| id | doaj-art-94fccba122624f5a8aefa2eeb570d3bd |
| institution | OA Journals |
| issn | 2666-951X |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Tetrahedron Chem |
| spelling | doaj-art-94fccba122624f5a8aefa2eeb570d3bd2025-08-20T02:35:50ZengElsevierTetrahedron Chem2666-951X2024-12-011210008910.1016/j.tchem.2024.100089(Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalystSamuel Redl0Christoph Topf1Institute of Catalysis (INCA), Johannes Kepler University, Altenbergerstraße 69, 4040, Linz, AustriaCorresponding author.; Institute of Catalysis (INCA), Johannes Kepler University, Altenbergerstraße 69, 4040, Linz, AustriaWe communicate a versatile and user-friendly Cu-based catalytic method that allows for the selective hydrogenation of enoates and alkynes. The introduced protocol is free from any ex ante modifications of the used Cu(I) precursors by air-sensitive phosphines or elaborate N-heterocyclic carbene ligands. The conjugate hydrogenation of enoates and the (selective) reduction of C≡C bonds is achieved through a [Cu(CH3CN)4]+/tert-butoxide pair whereby we describe a delicate influence of the base cation on the chemoselectivity of the respective transformation. In case of the ester-to-alcohol reduction, a combination of simple CuI and NaOtBu proved to be successful. Deuteration experiments are included to address certain mechanistic aspects of the introduced catalytic system. All requisite chemicals are readily obtainable through commercial channels and the catalyst assembly is set up on the bench without the need for special lab-technical precautions.http://www.sciencedirect.com/science/article/pii/S2666951X24000287Heterogeneous hydrogenationSelective reductionCopperN-Heterocyclic carbenesEnoatesAlkynes |
| spellingShingle | Samuel Redl Christoph Topf (Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst Tetrahedron Chem Heterogeneous hydrogenation Selective reduction Copper N-Heterocyclic carbenes Enoates Alkynes |
| title | (Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst |
| title_full | (Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst |
| title_fullStr | (Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst |
| title_full_unstemmed | (Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst |
| title_short | (Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst |
| title_sort | semi hydrogenation of enoates and alkynes effected by a versatile particulate copper catalyst |
| topic | Heterogeneous hydrogenation Selective reduction Copper N-Heterocyclic carbenes Enoates Alkynes |
| url | http://www.sciencedirect.com/science/article/pii/S2666951X24000287 |
| work_keys_str_mv | AT samuelredl semihydrogenationofenoatesandalkyneseffectedbyaversatileparticulatecoppercatalyst AT christophtopf semihydrogenationofenoatesandalkyneseffectedbyaversatileparticulatecoppercatalyst |