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An Anionic Mesoionic Carbene (anMIC) and its Transformation to Metallo MIC-Boranes: Synthesis and Properties.
Angew Chem Int Ed Engl
January 2025
Freie Universitat Berlin, Chemistry and Biochemistry, Fabeckstraße 34-36, 14195, Berlin, GERMANY.
Neutral mesoionic carbenes (MICs) based on a 1,2,3-triazole core have had a strong impact on various branches of chemistry such as homogeneous catalysis, electrocatalysis, and photochemistry/photophysics. We present here the first general synthesis of anionic mesoionic carbenes (anMICs) based on a 1,2,3-triazole core and a borate backbone. The free anMIC is stable in solution under an inert atmosphere at low temperatures, and can be stored for several weeks.
View Article and Find Full Text PDFFacile Synthetic Access Towards Sulfur- and Selenium-Functionalized Boron-Based Multiresonance TADF Emitters.
Molecules
December 2024
Department of Inorganic and Analytical Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
Thermally activated delayed fluorescence (TADF) materials with high photoluminescence quantum yields and a fast reverse intersystem crossing (RISC) are of the highest interest for organic light-emitting diodes (OLEDs). In the past decade, triaryl boranes with multiple resonance effect (MR) have captured significant attention. The efficiency of MR-TADF emitters strongly depends on small singlet-triplet energy gaps (ΔE), but also on large reverse intersystem crossing (RISC) rate constants (k).
View Article and Find Full Text PDFSelective Reduction of Esters to Access Aldehydes Using Fiddler Crab-Type Boranes.
J Am Chem Soc
January 2025
Organocatalysis Research Group, Institute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest H-1117, Hungary.
The partial reduction of esters to aldehydes is a fundamentally important transformation for the synthesis of numerous fine chemicals and consumer goods. However, despite the many efforts, limitations have persisted, such as competing overreduction, low reproducibility, use of exigent reaction conditions and hazardous chemicals. Here, we report a novel catalyst family with a unique steric design which promotes the catalytic partial reduction of esters with unprecedented, near-perfect selectivity and efficiency.
View Article and Find Full Text PDFSelective Synthesis of -Michael Acceptors via Hydroalkylation of Conjugated Alkynes.
J Am Chem Soc
January 2025
Department of Chemistry, University of Washington, Seattle, Washington 98195, United States.
Hydroalkylation of terminal alkynes is a powerful approach to the synthesis of disubstituted alkenes. However, its application is largely unexplored in the synthesis of α,β-unsaturated carbonyls, which are common among synthetic intermediates and biologically active molecules. The thermodynamically less stable -isomers of activated alkenes have been particularly challenging to access because of their propensity for isomerization and the paucity of reliable -selective hydroalkylation methods.
View Article and Find Full Text PDFBorane-Mediated Highly Secondary Selective Deoxyfluorination of Alcohols.
Angew Chem Int Ed Engl
December 2024
EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, EH9 3FJ, UK.
Organofluorine compounds are vital across multiple sectors, hence highly selective methods to install fluorine are of considerable importance. The deoxyfluorination of alcohols is a key approach to prepare organofluorine compounds, however, a highly secondary (2°)-selective deoxyfluorination of alcohols has not been realized to date. Herein, we report that borane-mediated deoxyfluorination results in high 2°-selectivity in inter- and intra-molecular competition reactions versus primary (1°), tertiary (3°) and even benzylic (Bn) alcohols.
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