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Copper-Catalyzed Intermolecular [2 + 2 + 2] Annulation of Diynes with Alkynes: Construction of Carbazoles.
Org Lett
January 2025
Key Laboratory of Chemical Biology of Fujian Province and State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
Transition-metal-catalyzed [2 + 2 + 2] annulation of alkynes is an efficient pathway for the synthesis of aromatic compounds. However, most of the established methods require noble metal catalysts. Herein, we report a copper-catalyzed intermolecular [2 + 2 + 2] annulation of diynes with alkynes through vinyl cation intermediates, enabling the atom-economical preparation of biologically important carbazole skeletons.
View Article and Find Full Text PDFAerobic oxidation of alkylarenes and polystyrene waste to benzoic acids a copper-based catalyst.
Chem Sci
December 2024
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University Changchun Jilin 130012 China
The chemical recycling of polystyrene (PS) waste to value-added aromatic compounds is an attractive but formidable challenge due to the inertness of the C-C bonds in the polymer backbone. Here we develop a light-driven, copper-catalyzed protocol to achieve aerobic oxidation of various alkylarenes or real-life PS waste to benzoic acid and oxidized styrene oligomers. The resulting oligomers can be further transformed under heating conditions, thus achieving benzoic acid in up to 65% total yield through an integrated one-pot two-step procedure.
View Article and Find Full Text PDFCopper-Catalyzed Asymmetric C(sp)-H Benzylation: Stereoselective Synthesis of Unnatural Aromatic Amino Acids.
Org Lett
December 2024
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou 730000, China.
The general synthesis of chiral unnatural aromatic amino acids has rarely been reported. We herein describe a visible light-promoted copper-catalyzed enantioselective C(sp)-H benzylation of glycine derivatives. The method demonstrated compatibility in coupling various -hydroxyphthalimide (NHP) esters derived from aromatic acids with glycine derivatives, providing a general protocol for synthesizing analogues of phenylalanine, tryptophan, and tyrosine.
View Article and Find Full Text PDFCopper-Catalyzed Difluoromethylation of Alkenyl Thianthrenium Salts.
Org Lett
December 2024
School of Chemistry and Chemical Engineering, Nanchang University, Nanchang, Jiangxi 330031, China.
Article Synopsis
- A new protocol has been developed for transforming alkenylsulfonium salts into difluoromethylated alkenes using copper catalysis and a specific reagent called the Vicic-Mikami reagent.
- This method allows for the selective synthesis of either aromatic or aliphatic difluoromethylated alkenes and can also be applied to perfluoroalkylation processes.
- The protocol is designed for large-scale synthesis, making it suitable for various applications in chemical production.
Recyclable Magnetic MOF-Catalyzed Synthesis of 1-Aminoisoquinolines and 6-Aminophenanthridines from 5-(2-Bromoaryl)tetrazoles and 1,3-Diketones under Microwave Irradiation.
J Org Chem
December 2024
Department of Applied Chemistry, Kyungpook National University, 80 Daehakro, Bukgu, Daegu 41566, Republic of Korea.
In this study, 5-(2-bromoaryl)tetrazoles were reacted with 1,3-diketones in DMF in the presence of a catalytic amount of magnetic Cu-MOF-74 (FeO@SiO@Cu-MOF-74) and a base under microwave irradiation to yield the corresponding 1-aminoisoquinolines. The FeO@SiO@Cu-MOF-74 catalyst could be easily recovered from the reaction mixture and reused four times without any significant loss of catalytic activity. An initial copper-catalyzed C(sp)-C(sp) bond formation accompanied by -Claisen deacylative cyclocondensation (for acyclic 1,3-diketones) and direct cyclocondensation (for cyclohexane-1,3-diones) is proposed as a key reaction pathway for this process.
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