An improved protocol where a pre-cursor, [Ru(Cl)(2)(NBD)(Py)(2)], is treated with ligands to form [RuCl(2)(bidentate ligand)(diamine)] pre-catalysts for ester hydrogenation is reported. This family of catalysts, as well as a range of ruthenium complexes of tridentate P^N^X (X = NR(2), OH) ligands have been investigated in the hydrogenation of aromatic esters. A range of aromatic esters can be hydrogenated in high yields at temperatures between 30 °C and 100 °C.
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http://dx.doi.org/10.1039/c2dt30973d | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Institut für Chemie, Carl von Ossietzky Universität Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26129, Oldenburg, Germany.
The iodination of electron-deficient arenes and heteroarenes is a long-standing problem in organic synthesis. Herein we describe the electrochemical iodination in nitromethane with BuNI as iodine source and supporting electrolyte under Lewis acid-free conditions in the presence of small amounts of chloride anions. The electrochemically generated reagent could be applied for the iodination of halogenated arenes, aromatic aldehydes, acids, esters, ketones, as well as nitroarenes to afford the products in good to excellent yields.
View Article and Find Full Text PDFCarbohydr Res
January 2025
Department of Biomolecular Sciences, University of Urbino "Carlo Bo", Campus Scientifico E. Mattei, via Ca' Le Suore 2, 61029, Urbino, PU, Italy. Electronic address:
Cinnamic Acid Sugar Ester Derivatives (CASEDs) are a class of natural compounds that exhibit several interesting biological activities. However, to date, no examples of their use in sunscreen formulations have been reported. Here, we describe the synthesis of a series of novel cinnamic acid esters of glucose (4a-g), ribose (4h) and lactose (4i) starting from the respective acetals 3.
View Article and Find Full Text PDFOrg Lett
January 2025
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China.
The transition metal-catalyzed coupling reaction has renewed the role of ester as an electrophilic partner. In this context, we describe a synergistic Ni/Zn-catalyzed formal transesterification reaction of but-3-enyl esters with tetrahydrofuran and alkyl iodides to give 4-alkoxylbutyl esters. The aromatic and aliphatic esters are both competent electrophiles and thus broaden the substrate scope of esters in coupling reactions, because the electrophiles in previously reported work were strictly limited to aromatic ones.
View Article and Find Full Text PDFChem Sci
January 2025
College of Chemistry and Chemical Engineering, Key (Guangdong-Hong Kong Joint) Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University Shantou 515063 P. R. China
In the past few years, the direct activation of organohalides by ligated boryl radicals has emerged as a potential synthetic tool for cross-coupling reactions. In most existing methods, ligated boryl radicals are accessed from NHC-boranes or amine-boranes. In this work, we report a new photocatalytic platform by modular assembly of readily available amines and diboron esters to access a library of ligated boryl radicals for reaction screening, thus enabling the cross-coupling of organohalides and alkenes including both activated and unactivated ones for C(sp)-C(sp) bond formation by using the assembly of DABCO A1 and BNepB1.
View Article and Find Full Text PDFOrg Lett
January 2025
School of Chemistry, Chemical Engineering and Life Science, Hubei Key Laboratory of Nanomedicine for Neurodegenerative Diseases, Wuhan University of Technology, Wuhan 430070, China.
A photoinduced copper-mediated acyloxylation of arylthianthrenium or arylphenoxathiinium salts with either aliphatic or aromatic carboxylic acids is described for the convenient synthesis of -aryl esters. The reaction has shown obvious advantages, such as high efficiency, good functional group tolerance, excellent chemoselectivity, and capacity for esterification of complex drug molecules, offering a practical synthetic route to multifunctionalized and sterically congested -aryl esters, which are potentially useful in the development of new prodrugs or twin drugs.
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