(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 ligands.The conjugate hydrogenation of enoates and the (selective) reduction of C ---C bonds is achieved through a [Cu(CH 3 CN) 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.semihydrogenation of alkynes [20-23], and enynes [24] to afford the

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Publication Details

Journal
Tetrahedron Chem
Published
2024-08-15
DOI
https://doi.org/10.1016/j.tchem.2024.100089
Citations
2
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
0.32

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article

(Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst

Christoph Topf, Samuel Redl
2 citations
Tetrahedron Chem
Asymmetric Hydrogenation and Catalysis
0.32
article

(Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst

Christoph Topf, Samuel Redl
article en
2 citations

Abstract

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(CH 3 CN) 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.semihydrogenation of alkynes [20-23], and enynes [24] to afford the

Tetrahedron ChemVol. 12
Johannes Kepler University of Linz (AT)
Institut National Du Cancer
Openalex Percentile: Top 50%
Asymmetric Hydrogenation and Catalysis
0.32
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(Semi)hydrogenation of enoates and alkynes effected by a versatile, particulate copper catalyst — Christoph Topf, Samuel Redl · Tetrahedron Chem (2024) | TGRS Research Map | TGRS