Terminal alkynes react with allylamine in the presence of a RhCl(PPh3)3 catalyst to give (E)-3-alkylidene-3,4-dihydro-2H-pyrroles. The products consist of two molecules of alkyne and one molecule of allylamine. Although dimers, trimers, and oligomers of alkynes are also obtained as byproducts, the addition of various ammonium salts to the reaction suppresses such oligomerization, resulting in an increase in product.
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http://dx.doi.org/10.1021/ol0619415 | DOI Listing |
Org Lett
January 2025
Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou, Guangdong 511436, China.
Presented herein is a nickel-catalyzed chemo- and regioselective three-component tandem carboamination and cyclization of terminal alkynes with organoboronic acids and anthranils for facile and modular access to 2,3-substituted quinolines. In this process, anthranil has dual roles: serving as an electrophilic aminating reagent and a redox buffer to suppress the generation of an off-cycle Ni(0) complex. Moreover, the anionic acetylacetonate (acac) ligand was found to be vital to ensure a productive Ni(I)-Ni(III)-Ni(I) catalytic cycle.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Instituto Universitario de Tecnología Química, Universitat Politècnica de València-Consejo Superior de Investigaciones Científicas, Universitat Politècnica de València, Av. De los Naranjos s/n, 46022 Valencia, Spain.
Due to their conductive properties and optoelectronic tunability, MXenes have revolutionized the area of electrocatalysis and active materials in supercapacitors. In comparison, there are only a few reports on MXenes as thermal catalysts for general organic reactions. Herein, the unprecedented catalytic activity of TiC MXene for the hydroamination of alkynes is reported, overcoming the limitations of poor activity, lack of selectivity, and stability, which are generally encountered in the solid catalysts known so far.
View Article and Find Full Text PDFInt J Biol Macromol
January 2025
Department of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China. Electronic address:
Zein and its complexes have been considered as promising carriers for encapsulating and delivering various biological active ingredients, however, there still have some issues about Zein-based drug delivery systems should be considered, including poor colloidal stability, low drug encapsulation efficiency as well as rapid initial drug release, and uncontrollable release. In this work, we reported for the first time that hyperbranched polymers (HPG) functionalized Zein with terminal alkyne (Zein-HPG-PA) can be used for loading anticancer agent curcumin (CUR) via a facile phenol-yne click reaction. The resultant product (Zein-HPG-PA@CUR) displays high drug loading capacity, small particle size and excellent water dispersibility.
View Article and Find Full Text PDFAsian J Org Chem
January 2025
Department of Medicinal Chemistry, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, New Jersey 08854, USA.
A one-pot process was developed to synthesize in moderate to high yield a series of 2-substituted indoles and 7-azaindoles starting from 2-iodo--mesylarylamines and terminal alkynes in the presence of CuO in DMF at 90-120 °C. Without isolation of any intermediate, our optimized conditions enabled the introduction of ester, phenyl, hydroxymethyl, hydroxyethyl, -Boc-aminomethyl, and methyl at the 2-postion of indoles and 7-azaindoles. The reaction tolerates a variety of substrates containing halogens, or acid- or base-sensitive functional groups without requiring a Pd catalyst, a ligand, or a base.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Sichuan University, State Key Laboratory of Biotherapy, CHINA.
Herein we report a cobalt-catalyzed hydroglycosylation of terminal alkynes, employing bench-stable ortho-iodobiphenyl (oIB) substituted sulfides as glycosyl donors. This reaction occurs with high stereo- and regioselectivity to afford E-configured vinyl α-C-glycosides, a class of compounds nontrivial to access by previous methods. The use of a bis(oxazoline) ligand with bulky side chains is critical for the high selectivities observed.
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