An efficient copper-catalyzed three-component tandem reaction of alkynes, α-diazo esters, and TMSN to construct triazoles has been developed. Through this strategy, a number of diverse N-substituted 1,2,3-triazoles were conveniently obtained in moderate to good yields from simple and readily available starting materials using KCO as the base. The mechanism of the tandem Cu-catalyzed azide-alkyne cycloaddition (CuAAC) and Cu-carbenoid-participated C-N coupling reaction has been investigated.
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http://dx.doi.org/10.1021/acs.joc.3c02112 | DOI Listing |
Org Lett
December 2024
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University, Changchun 130024, China.
A novel dual photoredox/copper-catalyzed three-component alkylcyanation of alkenes and 1,4-alkylcyanation of 1,3-enynes have been developed. In this radical cyanoalkylation reaction, the photoredox induced alkyl radical from sulfoxonium ylides adds to the carbon-carbon double bonds of styrenes or 1,3-enynes, and the generated benzylic or allenyl radicals couple with a Cu(II) cyanide complex to achieve selective cyanation. The reaction exhibits high chemo- and regioselectivity and a wide substrate scope, providing an efficient method for the synthesis of alkyl nitriles and allenyl nitriles in a single step.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China.
A one-pot, three-component synthesis of indole-benzofuran bis-heterocycles from terminal alkynes, salicylaldehydes, and indoles has been developed via copper-catalyzed tandem annulation. This catalytic system utilizes readily available starting materials, enabling predictable synthesis of indole-benzofuran bis-heterocycles with broad substrate versatility, excellent regiocontrol, and gram-scale amenability. The reaction proceeds via a sequential pathway involving A3 coupling, 1,4-conjugate addition, and 5-- cyclization.
View Article and Find Full Text PDFAcc Chem Res
December 2024
Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
J Am Chem Soc
November 2024
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Frontiers Science Center of Molecule Intelligent Syntheses, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
The direct use of readily available aldehydes as acyl radical precursors has facilitated diverse three-component acylative difunctionalization reactions of alkenes, offering a powerful route to synthesize β-branched ketones. However, asymmetric three-component acylative difunctionalization of alkenes with aldehydes still remains elusive. Here we report a copper-catalyzed asymmetric three-component radical acylarylation of vinylarenes with aldehydes and aryl boronic acids.
View Article and Find Full Text PDFChem Sci
October 2024
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 P. R. China
The asymmetric dicarbofunctionalization of alkenes a radical relay process can provide routes to diverse hydrocarbon derivatives. Three-component carboalkynylation, limited to particular alkyl halides and using readily available cycloketone oxime esters as redox-active precursors, is restricted by the available pool of suitable chiral ligands for broadening the redox potential window of copper complexes and simultaneously creating the enantiocontrol environment. Herein, we report a new hybrid tridentate ligand bearing a guanidine-amide-pyridine unit for photoinduced copper-catalyzed cyanoalkylalkynylation of alkenes.
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