A facile copper-catalyzed sustainable thiolation of ketones with sulfonohydrazides has been designed for the efficient construction of benzylic thioethers in excellent yield under mild reaction conditions. The current approach avoids the widely used thiolation reagent, thiols. The commercial availability of the base and reagents, broad substrate scope, and convenient reaction procedure make it an attractive method for benzylic thioether synthesis.
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http://dx.doi.org/10.1021/acs.joc.3c01598 | DOI Listing |
J Sep Sci
December 2024
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, China.
Chiral macrocycles have emerged as attractive media for chromatographic enantioseparation due to their excellent host-guest recognition properties. In this study, a new chiral stationary phase (CSP) based on 1,1'-binaphthyl chiral polyimine macrocycle (CPM) was reported. The CPM was synthesized by one-step aldehyde-amine condensation of (S)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxaldehyde with 1,2-phenylenediamine and bonded on thiolated silica via the thiol-ene click reaction to afford the CSP.
View Article and Find Full Text PDFInt J Biol Macromol
December 2024
Department of Chemistry, R.T.M. Nagpur University, Nagpur 440033, India. Electronic address:
Hexavalent chromium is known for high toxicity as well as carcinogenicity and leads to contamination of water bodies through various anthropogenic activities. Chitosan biopolymer has limited adsorption capacity towards this toxicant. In order to boost hexavalent chromium adsorption, diacetylmonoxime was used to modify thiolated chitosan.
View Article and Find Full Text PDFJ Org Chem
November 2024
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Manuel Lardizabal Pasealekua 3, Donostia-San Sebastian 20018, Spain.
While bicyclic isothiourea (ITU) moieties are found in biologically active molecules and organocatalysts, a catalytic asymmetric synthesis of ITUs is pending. Here, we report the catalytic, enantioselective functionalization of enolizable template with a variety of electrophiles, including unsaturated ketones, esters, sulfones, nitro compounds, and thiolating reagents, as an entry to enantioenriched bicyclic ITUs . Scope and limitations are shown, as well as examples of product derivatization.
View Article and Find Full Text PDFOrg Lett
October 2024
School of Chemistry and Chemical Engineering, Nanchang University, Nanchang, Jiangxi 330031, People's Republic of China.
We present the first example of nickel(II)-catalyzed β-C(sp)-H thiolation of ketones, employing 2-hydrazinopyridine as an efficient directing group. This approach enables the thiolation of a diverse array of ketones at the β-position. The straightforward installation and subsequent removal of the directing group significantly enhance the synthetic versatility and practicality of this transformation.
View Article and Find Full Text PDFJ Chromatogr A
September 2024
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, PR China.
Macrocycles play vital roles in supramolecular chemistry and chromatography. 1,1'-Bi-2-naphthol (BINOL)-based chiral polyimine macrocycles are an emerging class of chiral macrocycles that can be constructed by one-step aldehyde-amine condensation of BINOL derivatives with other building blocks. These macrocycles exhibit good characteristics, such as facile preparation, rigid cyclic structures, multiple chiral centers, and defined molecular cavities, that make them good candidates as new chiral recognition materials for chromatographic enantioseparations.
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