This paper reports a direct α-(hetero)arylation of acrylamides through an inverse electron-demand nucleophilic addition, specifically an -Michael-type addition. The introduction of a quinolyl directing group facilitates the nucleophilic addition of (hetero)arenes to the α-position of acrylamides. The quinolyl directing group effectively suppresses undesired β-hydrogen elimination and is removable for subsequent derivatization. The presented method provides an atom economical synthesis of α-(hetero)arylamide with a high degree of functional group tolerance.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/jacs.4c00841 | DOI Listing |
Chemistry
January 2025
University of Nottingham, The GSK Carbon Neutral Laboratories for Sustainable Chemistry, Jubilee Campus, Triumph Road, NG7 2TU, Nottingham, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
The nucleophilic propargylation of azinium ions with a propargylboronate proceeds efficiently under gold(I) catalysis. A range of N-alkylated pyridinium, quinolinium, and pyrazinium ions undergo propargylation with good yields and high regioselectivities to give various functionalized 1,4-dihydropyridines, 1,2-dihydropyridines, 1,4-dihydroquinolines, 1,2-dihydroquinolines, and 4,5-dihydropyrazines. No allenylation side-products are observed.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
Poly(vinyl chloride) (PVC) and polystyrene (PS) are among the least recycled plastics. In this work, we developed a simple and novel strategy to valorize PVC and PS plastics via photothermal conversion to (1-chloroethyl)benzene, a commodity chemical with excellent versatility. As PVC is known to release HCl gas and decompose into conjugated polyenes, we envisioned a dual role for PVC plastics.
View Article and Find Full Text PDFOrg Lett
January 2025
School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.
An iron(III)-mediated nucleophilic cascade cyclization of -propiolyl enamides with various diselenides was developed, which provides an efficient way to construct seleno-heterocycles. A mechanism study shows that the cascade process involves the selective addition of diselenides to the C≡C bond generating a seleniranium ion, followed by an intramolecular nucleophilic attack of enaminic carbon of tertiary enamide. Utilizing this protocol, a variety of 3-seleno-2-pyridones were successfully synthesized featuring good functional group compatibility and simple operation.
View Article and Find Full Text PDFMolecules
December 2024
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Zwitterionic π-allenyl palladium species are newly developed intermediates. A substrate-controlled step existed in the cycloaddition of zwitterionic π-allenyl palladium species with tropsulfimides or tropones. With the assistance of previously experimental studies, zwitterionic allenyl/propargyl palladium species was provenly found by HRMS.
View Article and Find Full Text PDFMolecules
December 2024
College of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, China.
Isochroman and azole moieties are both present in a wide variety of biologically active molecules. Their efficient combination under mild reaction conditions is beneficial for obtaining small-molecule drug candidates. In this paper, we describe electrochemical α-C(sp)-H/N-H cross-coupling reactions between isochromans and azoles, yielding products in moderate to excellent yields.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!