A revised pathway for the catalytic Staudinger amidation reaction is presented that involves the intervention of in situ-generated silyl esters as the species responsible for amidation.
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http://dx.doi.org/10.1039/c7cc03076b | DOI Listing |
Commun Chem
January 2025
National Institute of Chemistry, Hajdrihova 19, SI-1001, Ljubljana, Slovenia.
Iminophosphoranes with the general formula (RP═NR') have great potential in synthetic chemistry as valuable precursors/intermediates in organic synthesis or as building blocks for various organic compounds. However, the synthetic approaches and conditions to prepare iminophosphoranes are still poorly understood, limiting the utility of this chemistry for organic materials. In this article, a simple and efficient synthesis of previously unattainable poly(arylene iminophosphoranes) is reported.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Department of Chemistry, Johns Hopkins University; Baltimore, Maryland 21218, United States.
The trifluoromethyl (-CF) group represents a highly prevalent functionality in pharmaceuticals. Over the past few decades, significant advances have been made in the development of synthetic methods for trifluoromethylation. In contrast, there are currently no metalloenzymes known to catalyze the formation of C(sp)-CF bonds.
View Article and Find Full Text PDFAnal Chim Acta
November 2024
Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou, 450001, China. Electronic address:
Background: As an important reactive nitrogen species (RNS), HNO has been identified as an essential signaling molecule in many physiological processes. Ferroptosis produces a large amount of reactive oxygen species and reactive nitrogen species. However, the detailed mechanism of HNO during process of ferroptosis is rarely reported, especially in the near-infrared range.
View Article and Find Full Text PDFActa Pharm
September 2024
The Department of Pharmaceutical Chemistry, Faculty of Pharmacy University of Ljubljana, 1000 Ljubljana Slovenia.
In the final phases of bacterial cell wall synthesis, penicillin-binding proteins (PBPs) catalyze the cross-linking of peptidoglycan. For many decades, effective and non-toxic β-lactam antibiotics have been successfully used as mimetics of the d-Ala-d-Ala moiety of the natural substrate and employed as irreversible inhibitors of PBPs. In the years following their discovery, the emergence of resistant bacteria led to a decline in their clinical efficacy.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
Institute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
While azides do not react with simple alkenes except under harsh conditions, a diboron alkene analogue, the doubly cyclic alkyl(amino)carbene (CAAC)-stabilized dicyanodiborene 1, reacts spontaneously with organic azides (7-10 equiv.) at room temperature to yield two equivalents of stable CAAC-imino(cyano)boranes (2-R). NMR-spectroscopic monitoring of the reaction mixtures shows the initial formation of a 1 : 1 mixture of 2-R and a relatively long-lived intermediate (Int), which in the presence of excess azide is converted into a second equivalent of 2-R.
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