A Ni-Al bimetallic catalyzed enantioselective C-H exo-selective cyclization of imidazoles with alkenes has been developed. A series of bi- or polycyclic imidazoles with β-stereocenter were obtained in up to 98% yield and >99% ee. The bifunctional SPO ligand-promoted bimetallic catalysis proved to be critical to this challenging stereocontrol.
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http://dx.doi.org/10.1021/jacs.8b02547 | DOI Listing |
Nanoscale
December 2024
School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, China.
Multiple functional tailored materials have shown great potential for both pollutant degradation and freshwater recovery. In this study, we synthesized densely distributed Co onto carbon-layer-coated Ni/AlO hydrangea composites (Ni/AlO@Co) the polymerization of dopamine under a controlled graphitized process. The characterization results revealed that Ni/AlO@Co, with abundant exposed bimetallic Co-Ni species on the surface of AlO, could afford accessible catalytic sites for persulphate activation and subsequent pollutant degradation.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin, 300071, China.
Enantioselective transition metal-catalyzed C-H alkylation emerges as one of the most atom- and step-economical routes to chiral quaternary carbons, while big challenges still remain with acyl C-H alkylations. Herein, we use a Ni-Al bimetallic catalyst to facilitate a highly regioselective and highly enantioselective C-H alkylation of formamides with alkenes, constructing various oxindoles bearing a chiral quaternary carbon in up to 94 % yield and up to 95 % ee.
View Article and Find Full Text PDFACS Omega
July 2024
Department of Chemical Engineering, Faculty of Engineering, Mahidol University, Nakhon Pathom 73170, Thailand.
Developing a metallic catalyst for converting furfural (FAL) to highly valuable products such as cyclopentanone (CPO) is important for fine chemical synthesis by the efficient utilization of biomass resources. The presence of diverse unsaturated carbon atoms in FAL and the rearrangement of oxygen atoms hinder the production of CPO. We developed an optimal nickel (Ni)-to-platinum (Pt) molar ratio (1:0.
View Article and Find Full Text PDFJ Am Chem Soc
April 2024
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany.
The catalytic asymmetric construction of axially chiral C-N atropisomers remains a formidable challenge due to their low rotational barriers and is largely reliant on toxic, cost-intensive, and precious metal catalysts. In sharp contrast, we herein describe the first nickel-catalyzed atroposelective C-H alkylation for the construction of C-N axially chiral compounds with the aid of a chiral heteroatom-substituted secondary phosphine oxide (HASPO)-ligated Ni-Al bimetallic catalyst. A wide range of alkenes, including terminal and internal alkenes, were well compatible with the reaction, providing a variety of benzimidazole derivatives in high yields and enantioselectivities (up to 97:3 e.
View Article and Find Full Text PDFJ Org Chem
February 2024
Department of Chemistry, Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), College of Chemistry, Nankai University, Tianjin 300071, P. R. China.
The mechanism of the Ni-Al bimetallic-catalyzed C-H cyclization to construct tricyclic imidazoles is investigated using density functional theory calculations. The calculation result shows that the reaction mechanism involves sequential steps of substrate coordination, ligand-to-ligand hydrogen transfer (LLHT), and C-C reductive elimination to produce the final product tricyclic imidazole. The LLHT step is calculated to be the rate-determining step.
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