The dehydrogenative cross-coupling of arenes and alkenes is a particularly ideal approach for the synthesis of aryl alkenes. Herein, we report a photo-induced C-H/C-H cross-coupling between electron-rich arenes and styrene derivatives using a dual catalytic system containing an acridinium photosensitizer and a cobaloxime proton-reducing catalyst. This catalytic system enables the Csp-Csp bond formation accompanying H evolution. Various substituted aryl alkenes can be afforded with good to excellent yields and high β-regioselectivity.
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http://dx.doi.org/10.1039/c7sc04634k | DOI Listing |
IUCrdata
November 2024
Department of Chemistry, Kuwait University, PO Box 5969, Safat 13060, Kuwait.
The crystal structure of 1,4-bis-(neopent-yloxy)pillar[5]arene, CHNO (, featuring two encapsulated pyridine mol-ecules, reveals significant host-guest inter-actions. Inter-estingly, the pyridine guests are positioned near the neopent-yloxy substituents instead of the electron-rich aromatic core of the pillar[5]arene. This spatial arrangement suggests a preference for the pyridine mol-ecules to engage with the aliphatic regions of the host.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Tokyo Colledge, UT Institutes for Advanced Study, The University of Tokyo, Mitsui Link Lab Kashiwanoha 1, FS CREATION, 6-6-2 Kashiwanoha, Kashiwa, Chiba 277-0882, Japan.
This study reports a method for enhancing the functions and properties of traditional organic macrocyclic hosts by fully encapsulating them within a large ML cage to form host-in-host complexes. Within the cage host, the macrocyclic organic hosts with electron-rich aromatic rings, such as cyclotriveratrylene and calix[8]arene, adopt specific orientations enhancing their inherent molecular recognition abilities. Due to the high crystallinity of the ML cage, the guest encapsulation behavior of the host-in-host complexes can be observed by X-ray structural analysis.
View Article and Find Full Text PDFChem Asian J
November 2024
Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, China.
Since the initial report, the Friedel-Crafts reaction has become a powerful tool to functionalize arenes. Nevertheless, the use of nitrogen heterocycles as electrophiles in Friedel-Crafts reactions has been less explored. Here, we show a Friedel-Crafts-like reaction of electron-rich arenes with quinazolin-4(3H)-ones, enabling late-stage C2-H arylation of quinazolin-4(3H)-ones via triflic anhydride (TfO) activation.
View Article and Find Full Text PDFOrg Biomol Chem
November 2024
Department of Chemistry, Osmania University, Hyderabad-500 007, India.
A metal- and solvent-free, one-pot and TFA-promoted method for the construction of hetero/aryl-substituted quinoxalin-2-ones, pyrazin-2(1)-ones, and pyrimidin-4(3)-ones is reported. This method involves the reaction of chloro-derivatives of nitrogen heterocycles with electron-rich arenes/heteroarenes, followed by hydroxylation. This protocol is easy to use, providing access to (hetero)aryl-substituted -heterocycles in good yields.
View Article and Find Full Text PDFNat Commun
November 2024
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, PR China.
Photocatalytic N-to-C aryl migration allows for quick construction of highly useful amide derivatives from readily available compounds. By developing the reactions of sodium sulfinates with the N-aryl-propiolamides, we herein demonstrate that the CO-promoted visible-light-induced method enables a large variety of aryl groups on nitrogen atoms of the N-arylamides to undergo efficient aryl migration from N atom to C atom to synthesize tetra- and tri-substituted alkenyl amides selectively. 1,4-N-to-C aryl migration is a key step in this transformation which is achieved through photocatalytic radical-polar crossover pathway.
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