Copper-mediated chemoselective trifluoromethylation at the benzylic position by the use of shelf-stable electrophilic trifluoromethylating reagents 3 in good to high yields under mild conditions is described for the first time. The generality of this trifluoromethylation for a wide variety of benzyl bromides facilitates the rapid creation of structural diversity of medicinal candidates in drug discovery.
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http://dx.doi.org/10.1021/ol201205t | DOI Listing |
Angew Chem Int Ed Engl
December 2024
Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, 361005, P. R. China.
Reported herein is a convenient and efficient method for one-pot, catalytic reductive amination, as well as the first multi-component tandem reductive amination-functionalization of bench-stable and readily available common carboxylic esters. This method is based on the cationic [Ir(COD)]BArF-catalyzed chemoselective hydrosilylation of esters, followed by one-pot acid-mediated amination and nucleophilic addition. The reaction was conducted under mild conditions at a very low catalyst loading (0.
View Article and Find Full Text PDFOrg Lett
November 2024
Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017, P. R. China.
Green Chem
November 2024
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Universidade de Santiago de Compostela 15782 Santiago de Compostela Spain
-Difluoroalkenes and trifluoromethyl alkanes are prominent structures in biologically active compounds. Radical alkylation of α-trifluoromethyl alkenes represents a useful strategy to access these structures. However, reported methods have relied on the use of pre-functionalized radical precursors and examples involving the use of simple hydrocarbons as coupling partners are elusive.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2024
Department of Chemistry, Northwestern University, 2145N Sheridan Road, Evanston, IL, 60208, USA.
Here we present the first successful hydrotrifluoromethylation of unactivated olefins under electrochemical conditions. Commercially available trifluoromethyl thianthrenium salt (TT-CFBF , E=-0.85 V vs Fc/Fc) undergoes electrochemical reduction to generate CF radicals which add to olefins with exclusive chemoselectivity.
View Article and Find Full Text PDFOrg Lett
September 2024
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People's Republic of China.
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