We report the catalytic synthesis of 3-hydroxy-2-butanon (acetoin) from acetaldehyde as a key step in the synthesis of C-molecules from ethanol. Facile C-C bond formation at the α-carbon of the C building block is achieved using an N-heterocyclic carbene (NHC) catalyst. The immobilization of the catalyst on a Merrifield's peptide resin and its spectroscopic characterisation using solid-state Nuclear Magnetic Resonance (NMR) is described herein. The immobilization of the NHC catalyst allows for process intensification steps and the reported catalytic system was subjected to batch recycling as well as continuous flow experiments. The robustness of the catalytic system was shown over a maximum of 10 h time-on-stream. Overall, high selectivity S>90 % was observed. The observed deactivation of the catalyst with increasing time-on-stream is explained by ex-situ H solution-state, as well as C and N solid-state NMR spectra allowing us to develop a deeper understanding of the underlying decomposition mechanism of the catalyst.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11587688 | PMC |
| http://dx.doi.org/10.1002/cssc.202400647 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Bimetallic Cooperativity of a Ferrocene-based Iridium NHC Complex in Water Oxidation Catalysis: A New Frontier for Efficient Oxygen Evolution.
Chem Asian J
December 2024
CSIR - North East Institute of Science and Technology, Materials Sciences and Technology Division, Pulibor, CSIR-NEIST, 785006, Jorhat, INDIA.
Bimetallic catalysts have gained attention as promising contenders, owing to the synergistic interaction between two distinct metal centers. In this study, we present two N-heterocyclic carbene iridium(III) pentamethylcyclopentadienyl complexes [Cp*Ir(fcpyNHC)Cl]PF6 (1) and [Cp*Ir(pyNHC)Cl]PF6 (2) where 1 includes a ferrocene moiety acting as a bimetallic complex. Using ceric ammonium nitrate as a sacrificial oxidant, both complexes were tested for water oxidation.
View Article and Find Full Text PDFNaphthalene Hydrodearomatization via Controllable Photocatalytic Hydroboration.
J Org Chem
December 2024
College of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), Qingdao 266580, P. R. China.
The photocatalytic dearomative 1,4-hydroboration of naphthalenes with an N-heterocyclic carbene borane (NHC-BH) complex was reported herein with controllable regioselectivity and chemoselectivity. This protocol yielded a wide range of naphthalene derivatives bearing various functional groups, notably bioactive compounds. Hydroboration occurred through the cooperation of photoredox and hydrogen atom transfer via boryl radical addition to naphthalene and further selective protonation.
View Article and Find Full Text PDFVisible-Light-Mediated Radical -Hydroboration of Alkynes with NHC Borane.
J Org Chem
December 2024
School of Pharmaceutical Science, Hengyang Medical School, University of South China, Hengyang 421001, Hunan, China.
Although the radical hydroboration of alkenes with N-heterocyclic carbene (NHC) borane is well documented, the radical hydroboration of alkynes, especially terminal alkynes, remains challenging. Herein, a photoredox-catalyzed radical -hydroboration of alkynes with NHC borane has been developed, which provided various alkenyl boron compounds in moderate to good yields. This protocol exhibits a broad substrate scope, as both internal and terminal alkynes were compatible.
View Article and Find Full Text PDFElectroredox N-Heterocyclic Carbene-Catalyzed Enantioselective (3 + 3) Annulation of Enals with 2-Naphthols.
Org Lett
December 2024
Department of Chemistry, Indian Institute of Technology Ropar, Rupnagar, Punjab 140001, India.
Developing asymmetric transformations using electroredox and N-heterocyclic carbene (NHC)-catalyzed radical pathways is still desirable and challenging. Herein, we report an iodide-promoted β-carbon activation (LUMO-lowering process) of enals via electroredox carbene catalysis coupled with a hydrogen evolution reaction (HER). This strategy offers an environmentally friendly and sustainable route for rapidly assembling synthetically useful chiral naphthopyran-3-one in good to excellent yield and enantioselectivity using traceless electrons as inexpensive and greener oxidants.
View Article and Find Full Text PDFSynthesis, Luminescence, and Electrochemistry of Tris-Chelate Platinum(IV) Complexes with Cyclometalated N-Heterocyclic Carbene Ligands and Aromatic Diimines.
Inorg Chem
December 2024
Departamento de Química Inorgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, 19, 30100 Murcia, Spain.
Dicationic, -symmetrical, tris-chelate Pt(IV) complexes of general formula [Pt(trz)(N∧N)](OTf), bearing two cyclometalated 4-butyl-3-methyl-1-phenyl-1-1,2,3-triazol-5-ylidene (trz) ligands and one aromatic diimine [N∧N = 2,2'-bipyridine (bpy, ), 4,4'-di--butyl-2,2'-bipyridine (dbbpy, ), 4,4'-dimethoxi-2,2'-bipyridine (dMeO-bpy, ), 1,10-phenanthroline (phen, ), 4,7-diphenyl-1,10-phenanthroline (bphen, ), dipyrido[3,2-:2',3'-]phenazine (dppz, ), or 2,3-diphenylpyrazino[2,3-][1,10]phenanthroline (dpprzphen, )] are obtained through chloride abstraction from [PtCl(trz)] () using AgOTf in the presence of the corresponding diimine. Complexes show long-lived phosphorescence from LC excited states involving the diimine ligand, with quantum yields that reach 0.18 in solution and 0.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!