The direct cross-couplings of aryl nonaflates with aryl bromides could be successfully accomplished by utilizing nickel as the catalyst, magnesium as the metal mediator, and lithium chloride as the additive. The reactions proceeded efficiently in THF at room temperature to produce the desired biaryls in moderate to good yields, showing both a reasonable substrate scope and functional group tolerance. Additionally, an equally good performance could be realized when the reaction was subjected to scale-up synthesis. Preliminary study suggested that the reaction presumably proceeds through the in situ formation of an arylmagnesium reagent as the key reaction intermediate.
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http://dx.doi.org/10.1021/acs.joc.4c02777 | DOI Listing |
J Org Chem
January 2025
Technical Institute of Fluorochemistry (TIF), School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
The direct cross-couplings of aryl nonaflates with aryl bromides could be successfully accomplished by utilizing nickel as the catalyst, magnesium as the metal mediator, and lithium chloride as the additive. The reactions proceeded efficiently in THF at room temperature to produce the desired biaryls in moderate to good yields, showing both a reasonable substrate scope and functional group tolerance. Additionally, an equally good performance could be realized when the reaction was subjected to scale-up synthesis.
View Article and Find Full Text PDFMolecules
January 2025
Sustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.
A pyridine-fused triazapentalene shows weak fluorescence in solution and is readily accessible via nitrene-mediated cyclization. In this study, a modified Cadogan reaction was used to synthesize . Palladium-catalyzed reactions have been used as post-functionalization methods.
View Article and Find Full Text PDFNat Chem
January 2025
Department of Chemistry, Scripps Research, La Jolla, CA, USA.
Amino alcohols are vital in natural products, pharmaceuticals and agrochemicals, and as key building blocks for various applications. Traditional synthesis methods often rely on polar bond retrosynthetic analysis, requiring extensive protecting group manipulations that complicate direct access. Here we show a streamlined approach using a serine-derived chiral carboxylic acid in stereoselective electrocatalytic decarboxylative transformations, enabling efficient access to enantiopure amino alcohols.
View Article and Find Full Text PDFHeliyon
December 2024
Department of Chemistry, College of Engineering and Physical Sciences, Khalifa University of Science and Technology, Abu Dhabi, P.O. Box 127788, United Arab Emirates.
Suzuki-Miyaura coupling (SMC), a crucial C-C cross-coupling reaction, is still associated with challenges such as high synthetic costs, intricate work-ups, and contamination with homogeneous metal catalysts. Research intensely focuses on strategies to convert homogeneous soluble metal catalysts into insoluble powder solids, promoting heterogeneous catalysis for easy recovery and reuse as well as for exploring greener reaction protocols. Metal-Organic Frameworks (MOFs), recognized for their high surface area, porosity, and presence of transition metals, are increasingly studied for developing heterogeneous SMC.
View Article and Find Full Text PDFChem Sci
November 2024
KTH Royal Institute of Technology, Department of Chemistry Teknikringen 30 10044 Stockholm Sweden
We report on the synthesis of [2]rotaxanes from vicinal diols through dynamic covalent boronic ester templates, as well as the use of the boronic ester for rotaxane post-functionalisation. A boronic acid pincer ligand with two alkene-appended arms was condensed with a linear diol-containing thread, and ring-closing metathesis established a pre-rotaxane architecture along with a non-entangled isomer. Advanced NMR spectroscopy and mass spectrometry unambiguously assigned the isomers and revealed that the pre-rotaxane was in equilibrium with its hydrolyzed free [2]rotaxane form.
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