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A new trifluoroacetylation reagent was developed by using inexpensive and readily available trifluoroacetic anhydride and -phenyl-4-methylbenzenesulfonamide for the first time. The reaction of (het)aryl boronic acids with the new trifluoroacetylation reagent, -phenyl--tosyltrifluoroacetamide, proceeded smoothly in the presence of a palladium catalyst to provide trifluoromethyl ketones in satisfactory to excellent yields. Various groups, including the synthetically useful functional groups Cl, TMS, and PhCO, were tolerated well under the current reaction conditions. This new trifluoroacetylation reagent can be used in the large-scale synthesis of trifluoromethyl ketones, even at a low palladium catalyst loading.
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http://dx.doi.org/10.1021/acs.orglett.4c02689 | DOI Listing |
J Org Chem
August 2025
College of Chemistry, Zhengzhou University, Zhengzhou 450001, China.
A novel visible-light-driven method for the trifluoroacetylation of azauracils was reported, utilizing oxygen as the oxidant and a masked trifluoroacetyl reagent as the radical precursor. This eco-friendly approach eliminates the need for expensive catalysts, transition metals, and additional additives, offering a straightforward, efficient, and scalable solution. The method demonstrates excellent functional group tolerance and versatility, making it ideal for late-stage modifications of a wide range of bioactive molecules.
View Article and Find Full Text PDFChembiochem
April 2025
State Key Lab of Synthetic Biology, School of Life Sciences, Faculty of Medicine, Tianjin University, Tianjin, 300072, China.
Protein-based probes constructed via genetically encoding acetyl lysine (AcK) or its close analogs represent an important way to detect protein lysine deacetylases. Existing reported probes exhibit excellent sensitivity to NAD-dependent sirtuins but lack responsiveness to Zn-dependent histone deacetylases (HDACs). Herein, we reformed the probe design by replacing the genetically encoded AcK with trifluoroacetyl lysine (TfAcK) and generated fluorescent and bioluminescent probes that could respond specifically to HDAC8 recombinantly expressed in E.
View Article and Find Full Text PDFOrg Biomol Chem
February 2025
Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, P. R. China.
A strategy for trifluoroacetylation of quinoxaline-2(1)-ones has been investigated. This strategy employs masked trifluoroacyl reagents to obtain trifluoroacetylated quinoxaline-2(1)-ones under metal-, catalyst-, and light-free conditions. This approach is distinguished by its functional group compatibility and tolerance, as well as the simplicity of the experimental process, making it suitable for gram-scale synthesis.
View Article and Find Full Text PDFJ Mater Chem B
October 2024
Department of Chemistry, Birla Institute of Technology and Science-Pilani (Hyderabad Campus), Hyderabad-500078, India.
The human serum albumin (HSA) level is a valuable indicator of an individual's health status. Therefore, its detection/estimation can be used to diagnose several diseases. In this work, we have developed a series of donor-π-acceptor probes, which were found to selectively detect HSA over BSA (bovine serum albumin).
View Article and Find Full Text PDFOrg Lett
August 2024
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China.
A new trifluoroacetylation reagent was developed by using inexpensive and readily available trifluoroacetic anhydride and -phenyl-4-methylbenzenesulfonamide for the first time. The reaction of (het)aryl boronic acids with the new trifluoroacetylation reagent, -phenyl--tosyltrifluoroacetamide, proceeded smoothly in the presence of a palladium catalyst to provide trifluoromethyl ketones in satisfactory to excellent yields. Various groups, including the synthetically useful functional groups Cl, TMS, and PhCO, were tolerated well under the current reaction conditions.
View Article and Find Full Text PDF