Phosphine coordinated copper(I)-N-heterocyclic carbene complexes have emerged as an efficient material in catalysis and light-emitting applications. In this study, a gentle and sustainable approach to the copper(I)-carbene phosphine complexes is reported through an efficient C=Se activation protocol. The complexes [(Py^NHC)Cu(PPh ) ]X, X=BF (1), ClO (2), PF (3) and OTf (4); Py^NHC=3-isopropyl-1-(pyridin-2-yl)-imidazol-2-ylidene, and [(Py^NHC)Cu(PPh )(X)], X=Br (5) and I (6) have been synthesized by treating 1-isopropyl-3-(pyridin-2-yl)-imidazole-2-selone with corresponding copper(I) precursors and triphenylphosphine. In this synthetic strategy, N-heterocyclic carbene gets transferred from N-heterocyclic selone through a C=Se bond cleavage reaction to form copper(I) complexes within five minutes at room temperature. In addition, the mechanism responsible for the C=Se bond cleavage reaction has been fully investigated. These reactions are not sensitive to moisture and oxygen.
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http://dx.doi.org/10.1002/asia.202300217 | DOI Listing |
Nat Commun
January 2025
School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, China.
Stereocontrolled construction of tetrasubstituted olefins has been an attractive issue yet remains challenging for synthetic chemists. In this manuscript, alkynyl selenides, when treated with ArBCl, are subject to an exclusive 1,1-carboboration, affording tetrasubstituted alkenes with excellent levels of E-selectivity. Detailed mechanistic studies, supported by DFT calculations, elucidates the role of selenium in this 1,1-addition process.
View Article and Find Full Text PDFJ Agric Food Chem
January 2025
Ankang Research and Development Center for Se-Enriched Products, Ankang 725000, China.
Selenopeptides can be ideal dietary selenium (Se) supplements for humans. Currently, rice is not used much as a source of selenopeptides. Here, we executed the selenopeptidomics analysis of selenium-enriched rice protein hydrolysates using the full MS-dd-MS2 acquisition method and identified selenopeptides, including L{Se-Met}AK and other selenopeptides.
View Article and Find Full Text PDFOrg Lett
January 2025
School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
The translocation of an aryl group from selenium into carbon enabled by the cleavage of the C-Se bond is reported by using nitrogen atom-linked 1,7-diynes and diaryl diselenides as starting materials, leading to various selenophene derivatives in a regioselective manner. This method enables the construction of two C-Se bonds and two C-C bonds through sequential radical bicyclization and 1,2-aryl migration under metal-free conditions. Control experiments and mechanistic studies suggest that this reaction proceeds through the cleavage of the inert C(Ph)-Se bond, facilitating the aryl translocation process.
View Article and Find Full Text PDFEur J Med Chem
January 2025
Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266071, China. Electronic address:
The emergence of New Delhi metallo-β-lactamase-1 (NDM-1) poses a significant threat to the clinical application of antibiotics, as it possesses the ability to hydrolyze nearly all β-lactam antibiotics. Regrettably, there are currently no clinical drugs targeting NDM-1, making it imperative to develop highly potent and minimally toxic NDM-1 inhibitors. Herein, a series of molecular Trojan horses targeting NDM-1 were synthesized by introducing ebselen into 7-aminocephalosporanic acid derivatives via a C-Se bond.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Secció de Química Inorgànica, Departament de Química Inorgànica i Orgànica, Universitat de Barcelona, Martí i Franquès 1-11, 08028, Barcelona, Spain.
The preparation of organochalcogens has increased in recent times due to their promising biological activity properties. This work studies the reaction mechanism of a nickel(0)-catalyzed cross-coupling between benzonitrile and propanethiol to produce new C-S bonds by computational means. The proposed mechanism follows the classical oxidative addition/transmetalation/reductive elimination cross-coupling sequence, involving an unusual oxidative addition of a Ph-CN bond onto the active species.
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