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C-H Alkylation of Heterocycles via Light-Mediated Palladium Catalysis.
Angew Chem Int Ed Engl
October 2024
RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, D-52074, Aachen, Germany.
Article Synopsis
- Direct C-H alkylation of heterocycles is crucial for modifying natural products and pharmaceuticals, but there's a lack of versatile methods using common alkyl sources.
- The study presents a straightforward palladium-catalyzed method that utilizes alkyl halides under visible light, allowing for effective scalability and tolerance of various functional groups.
- The proposed mechanism involves a series of reactions including the addition of alkyl radicals, base-assisted deprotonation, and oxidation, supported by both experimental and computational approaches.
Photoinduced Palladium-Catalyzed Radical Germylative Arylation of Alkenes with Chlorogermanes.
J Org Chem
September 2024
College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, Hangzhou, 311121, Zhejiang, P. R. China.
Article Synopsis
- - The study presents a method for creating germanium-substituted indolin-2-ones using a palladium catalyst and chlorogermanes, triggered by visible light.
- - This process takes place under mild conditions and produces good to excellent yields, making it a convenient approach for synthesizing these compounds.
- - A critical aspect of the method involves activating germanium-chloride bonds with a palladium complex under light, with supporting evidence for germanium radicals provided through electron paramagnetic resonance spectroscopy.
Photoinduced Palladium-Catalyzed 1,2-Aminoalkylation of Aromatic Alkenes with Hydroxyl as the Directing Group.
Org Lett
June 2024
Henan University of Chinese Medicine, Zhengzhou 450046, China.
The hybrid nature of Pd(I)-alkyl radical species has enabled a wide array of radical-based transformations. However, in this transformation, the secondary Pd(I)-alkyl radical species are prone to recombining into Pd(II)-alkyl species to give Heck-type products via β-H loss. Herein, we report a visible-light-induced, three-component Pd-catalyzed 1,2-aminoalkylation of alkenes with readily available alkyl halides and amines to construct C-C and C-N bonds simultaneously.
View Article and Find Full Text PDFPhotoinduced Palladium-Catalyzed Radical Heck-Type Coupling of Cyclobutanone Oxime Esters with Vinyl Arenes.
J Org Chem
May 2024
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, 21 Gehu Road, Changzhou 213164, China.
A palladium-catalyzed radical Heck-type coupling reaction of cyclobutanone oxime esters with olefins under visible-light irradiation has been developed. The cyanoalkyl/Pd(I) hybrid species generated by selected ring-opening C-C bond cleavage of imino/Pd(I) species reacted smoothly with vinyl arenes, delivering the cyanoalkylation olefins under mild conditions. This elegant strategy has a broad scope and functional group tolerance.
View Article and Find Full Text PDFAccessing Benzoazepine Derivatives via Photoinduced Radical Relay Formal [5 + 2] Reaction of Amide/Alkyne Enabled by Palladium Catalysis.
Org Lett
April 2024
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, 21 Gehu Road, Changzhou 213164, China.
A novel class of alkyne-tethered amides facilitates an unprecedented photoinduced palladium-catalyzed radical relay formal [5 + 2] reaction. This innovative strategy allows for the rapid construction of diverse fused benzoazepine structures, yielding structurally novel and compelling compounds. With a broad substrate scope and excellent functional group tolerance, the methodology synthesizes biologically active compounds.
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