The monoamination of vicinal diols in the presence of in situ generated ruthenium catalysts has been investigated. Among the various phosphines tested in combination with [Ru(3)(CO)(12)], N-phenyl-2-(dicyclohexyl-phosphanyl)pyrrole showed the best performance. After optimization of the reaction conditions this system was applied to different secondary amines and anilines as well as a number of vicinal diols. With the exception of ethylene glycol, monoamination of the vicinal diols occurred selectively and the corresponding amino alcohols were obtained in good yields, producing water as the only side product.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1002/cssc.200900034 | DOI Listing |
RSC Adv
December 2024
Pharmacy, Cosmetic Chemistry and Biotechnology Research Group, Łukasiewicz Research Network-Industrial Chemistry Institute Rydygiera 8 01-793 Warsaw Poland +48 453 056 175.
A critical evaluation of the feasibility of a previously published method for synthesising halomethyl carbinols from carbonyl compounds and CHBr or CHCl using a bimetallic TiCl-Mg complex is presented. The synthesis of compounds lacking the -CH- group in their structure was achieved by following the procedures proposed in the reference literature or by introducing modifications to selected process parameters. These compounds were not identified as expected β-halohydrins but as products of reductive dimerisation or subsequent pinacolic rearrangement of carbonyl substrates.
View Article and Find Full Text PDFChemistry
December 2024
Indian Institute of Technology Kanpur, Department of Chemistry, IIT, Kanpur, 208 016, Kanpur, INDIA.
Porous organic polymers (POPs) are novel emergent materials for heterogeneous organocatalysis owing to their remarkable physicochemical stabilities. Through a bottom-up approach entailing diligent design of twisted biaryl building blocks with in-built o-iodobenzoic acid (IA) moieties, a series of POP precatalysts, p-OMeIA-POP, DiMeIA-POP, and m-OMeIA-POP, were synthesized by employing Friedel-Crafts alkylation. These IA-POP precatalysts can undergo in situ oxidation in the presence of Oxone® to generate hypervalent iodine(V) species (λ5-iodanes), in particular, modified o-iodoxybenzoic acid, popularly termed IBX, which mediates diverse oxidative transformations.
View Article and Find Full Text PDFChem Sci
November 2024
KTH Royal Institute of Technology, Department of Chemistry Teknikringen 30 10044 Stockholm Sweden
We report on the synthesis of [2]rotaxanes from vicinal diols through dynamic covalent boronic ester templates, as well as the use of the boronic ester for rotaxane post-functionalisation. A boronic acid pincer ligand with two alkene-appended arms was condensed with a linear diol-containing thread, and ring-closing metathesis established a pre-rotaxane architecture along with a non-entangled isomer. Advanced NMR spectroscopy and mass spectrometry unambiguously assigned the isomers and revealed that the pre-rotaxane was in equilibrium with its hydrolyzed free [2]rotaxane form.
View Article and Find Full Text PDFMolecules
October 2024
College of Life Sciences, Sichuan Normal University, Chenglong Avenue, Chengdu 610101, China.
Int J Biol Macromol
November 2024
Henan Key Laboratory of Biomarker Based Rapid-detection Technology for Food Safety, Food and Pharmacy College, Xuchang University, Xuchang 461000, PR China. Electronic address:
(2,3)-Butanediol dehydrogenases (BDHs) are widely utilized for the stereoselective interconversion between α-hydroxy ketones and vicinal diols to produce various functional building blocks. In this study, to enhance the specific activity towards (R)-phenyl-1,2-ethanediol (1a) for 2-hydroxyacetophenone (1b), the substrate-binding pocket of a Bacillus subtilis BDH (BsBDHA) was refined through site-directed mutagenesis. Based on molecular docking simulations, 14 residues were identified and subjected to alanine scanning mutagenesis.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!