A recyclable protocol using a CeO-nanorod catalyst for borylation of alkyl halides with Bpin (pin = OCMeCMeO) is reported. A wide range of synthetically useful alkyl boronate esters are readily obtained from primary and secondary alkyl electrophiles, including unactivated alkyl chlorides, demonstrating broad utility and functional group tolerance. Preliminary investigation revealed an involvement of in situ formed catalytically active boryl species. The catalyst can be reused for up to six runs without appreciable loss in activity. In addition, we have demonstrated the use of this recyclable catalyst for the borylation of aryl halides with Bpin, providing valuable aryl boronate esters under neat conditions.
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http://dx.doi.org/10.1021/acs.joc.3c01755 | DOI Listing |
Chem Commun (Camb)
January 2025
School of Chemistry and Chemical Engineering, Henan Key Laboratory of Boron Chemistry and Advanced Materials, Henan Normal University, Xinxiang, Henan 453007, China.
A series of N-Het·BH and AAE·BH complexes were prepared in moderate to high yields and the single-crystal structures of products 3, 31, 34, and 59 were determined. The N-Het·BH and AAE·BH complexes possess high stability, endowing these products with potential applications in luminescent and boron-containing drugs. The optical properties of the representative products have been preliminarily studied.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry and School of Pharmacy, China State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Here we present a regio- and stereoselective alkylation approach for unprotected saccharides using synergistic boronic acid and photoredox catalysis. Targeting the equatorial C-H bond of the -1,2-diol motif, this method employs MeB(OH) as a catalyst. Mechanistic investigations indicate that the formation of a tetracoordinate boron species, resulting from the interaction between the cyclic boronic diol ester and a free hydroxyl group in the saccharide, is critical to this transformation.
View Article and Find Full Text PDFTalanta
January 2025
State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin, 130022, China. Electronic address:
Flavonoid glycosides are formed by dehydration condensation of aglycones and sugar molecules. Therefore, discrimination of flavonoid glycosides from their corresponding aglycones is a challenging task because they contain the same aglycone part in their molecular structures. Herein, boric acid-functional Eu(III)-organic framework (BA-Eu-MOF) was applied to discriminate flavonoid glycosides including baicalin (Bai), wogonoside (Wog), rutin (Rut), puerarin (Pue), quercitrin (Que) and astragalin (Ast) from their corresponding aglycones for the first time.
View Article and Find Full Text PDFJ Nanobiotechnology
January 2025
Integrative Science Center of Germplasm Creation in Western China (Chongqing) Science City, Biological Science Research Center, Southwest University, Chongqing, 400715, China.
Significant progress has been made in the development of potential therapies for diseases associated with inflammation and oxidative stress. Nevertheless, the availability of effective clinical treatments remains limited. Herein, we introduce a novel silk-based bioactive material, TPSF, developed by sequentially conjugating Tempol and phenylboronic acid pinacol ester to silk fibroin.
View Article and Find Full Text PDFACS Appl Mater Interfaces
January 2025
State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Shanghai Engineering Research Center of Nano-Biomaterials and Regenerative Medicine, College of Biological Science and Medical Engineering, Donghua University, Shanghai 201620, China.
To simplify the composition and improve the efficacy of metal-phenolic network (MPN)-based nanomedicine, herein, we designed an MPN platform to deliver programmed death ligand-1 (PD-L1) antibody (anti-PD-L1) for combined tumor chemo/chemodynamic/immune therapy. Here, generation 5 poly(amidoamine) dendrimers conjugated with gossypol (Gos) through boronic ester bonds were used as a synthetic polyphenol to coordinate Mn, and then complexed with anti-PD-L1 to obtain the nanocomplexes (for short, DPGMA). The prepared DPGMA exhibited good water dispersibility with a hydrodynamic size of 166.
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