Stefan Jopp

Stefan Jopp
University of Rostock · Department Leben, Licht and Materie

Dr. rer. nat.

About

21
Publications
1,317
Reads
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145
Citations
Introduction
A researcher interested in the sweet chemistry of carbohydrates! I currently work as a Research Group Leader at the University of Rostock, where I also did my bachelor and master degrees as well as my PhD. In my post-doc phase I visited Tottori University, Japan, as a JSPS fellow. My current research is located in the area carbohydrate chemistry. My working group focuses on diverse applications of carbohydrate based ionic liquids, including polymers, biocatalysis, organocatalysis and more.
Additional affiliations
February 2020 - August 2020
Tottori University
Position
  • PostDoc Position
Description
  • Development of Ionic Liquids based on Glucosamine
July 2018 - present
University of Rostock
Position
  • PostDoc Position
Description
  • Carbohydrate Research
October 2014 - December 2015
Leibniz Institute for Catalysis
Position
  • Research Assistant
Description
  • Development of new Organocatalytic Procedures based on Phosphane Catalysts
Education
April 2016 - April 2018
University of Rostock
Field of study
  • Total Synthesis of new Dabigatran derivatives and Palladium catalysed reactions of Estrones
October 2012 - September 2014
University of Rostock
Field of study
  • Sonogashira reactions of Trifluoromethylquinolines
October 2009 - September 2012
University of Rostock
Field of study
  • Palladium catalysed CH activation of Pyrrols

Publications

Publications (21)
Article
Full-text available
The large pool of naturally occurring carbohydrates with their diversity in chirality and structure led to the idea of a systematic investigation of carbohydrate based ILs. To this end, we investigated the influence of different ether groups, mainly methyl or ethyl ether, on the secondary OH groups as well as different configurations on physical pr...
Article
Full-text available
Carbohydrate based ionic liquids (CHILs) are a sub‐class of ionic liquids which first emerged in 2007 and has since then attracted a steadily growing community of organic chemists. Since carbohydrates are naturally occurring materials with a broad spectrum of diastereomers, they are fitting materials for ionic liquids bearing stereochemical informa...
Article
Full-text available
In this article the authors investigated a new synthetic strategy to convert glucosamine, a natural resource produced from chitin, into several trimethylammonium glucosamine salts. The thermal properties of the new carbohydrate based ionic liquids (CHILs) have been measured to further investigate the structure‐property relationships. The authors fu...
Article
Full-text available
Hygroscopic effects in ionic liquids and salts in general, and how to suppress said hygroscopy, often needs to be considered during the everyday work routine. Chemicals that decompose, undergo hydrolysis or in any way change their composition when exposed to air are generally not considered to be bench-stable. In this study, we synthesized a low-hy...
Article
Full-text available
A series of novel ionic liquids based on glucose was synthesized in high yields in simple two or three‐step reaction procedures. These carbohydrate‐based ionic liquids were studied and compared to commercially available imidazolium‐based ionic liquids as supports for Novozym 435 in the acrylation of n‐butanol. A direct correlation between the avail...
Poster
Full-text available
The poster shows the two-step synthesis to a sugar-based monomer that is crosslinked to a hydrogel and the charaterization of hydrogels with different crosslinker concentrations and in different media.
Poster
Full-text available
The presented poster gives an overview of our studies on common ionic liquids and carbohydrate based ionic liquids as supports for Novozym 435, an common biocatalyst containing Candida antarctica lipase B.
Article
Full-text available
The title solvated molecular salt, [MeGluVIm]I (MeGluVIm = 1-(methyl-α-D-glucopyranosid-6-yl)-3-vinylimidazolium), or C 12 H 19 N 2 O 5 ⁺ ·I ⁻ ·C 3 H 7 NO, was synthesized from methyl-α-D-6-iodoglucopyranoside and vinylimidazole in DMF. It crystallizes through precipitation from ethyl acetate solution directly after the reaction procedure. The crys...
Article
Full-text available
Acridine derivatives have attracted considerable interest in numerous areas owing to their attractive physical and chemical properties. Herein, starting from readily available anthranilic acid, an efficient synthesis of 2,4-bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridine derivatives was accomplished via a one-pot double Sonogashira cross-coupl...
Article
The authors of this work have successfully synthesized a broad choice of new ribose based ionic liquids, using several varying protecting groups (methyl, ethyl, allyl and benzyl) at the various positions of the carbohydrate, as well as different quarternised N-heterocycles and different anions. These consistent variations of the carbohydrate based...
Cover Page
Full-text available
CHILs! A series of carbohydrate‐based ionic liquids have been successfully synthesized from glucosamine, an abundant and regrowing resource, which can be obtained through shell refinery from chitin and chitosan. The synthesis of these CHILs is straightforward and performed in high yields. Their thermal properties as well as their potential as catal...
Article
The total synthesis of a new dabigatran derivative featuring a tosyl protecting group at the amidine group of dabigatran was explored. During the course of this work, different new synthetic pathways towards dabigatran intermediates are investigated and known concepts revisited. In this context, it was found that, in our hands, a published synthesi...
Article
A catalytic system for the chlorination of alcohols under Appel conditions was developed. Benzotrichloride is used as a cheap and readily available chlorinating agent in combination with trioctylphosphane as the catalyst and phenylsilane as the terminal reductant. The reaction has several advantages over other variants of the Appel reaction, e.g. n...
Article
A straightforward, site-selective arylation of the bis(triflate) of estrone by Suzuki–Miyaura reactions has been developed. Monoarylation occurs selectively at the D-ring with good to excellent yield. Such products were exemplarily employed for the synthesis of estrones containing two different aryl substituents.
Article
4-Bromo-3-O-triflyl-estrone has been synthesized in 2 steps from estrone and was successfully employed in chemoselective palladium catalysed Suzuki-Miyaura reactions. Mono- and bis-arylations were carried out selectively by variation of ligands and solvents. Overall 19 derivatives of mono- and bis-arylated estrones were synthesized under optimized...
Article
The Suzuki-Miyaura reactions of 16-E-(triflyloxymethylidene)-3-methoxy-α-estrone allow for a convenient synthesis of various 16-E-(arylidene)-3-methoxy-α-estrones in good to high yields and with excellent E-selectivity. Both electron-rich and electron-poor boronic acids could be successfully employed.
Poster
Full-text available
The presented poster gives a short summary of three projects on 16-Methylidene-Estrones and their palladium catalysed functionalisation via Mizoroki-Heck-, Sonogashira- and Suzuki-Miyaura reactions. All three projects have been published individually.
Article
Sonogashira reactions of steroids have been studied. The reaction of α-estron-16-methylidenyloxy triflate with various alkynes afforded novel alkynylvinylidene steroids. The reactions proceeded in good to quantitative yields, with excellent E-selectivity and with a broad synthetic scope.
Article
16-E-Arylidene-3-methoxy-estrones were synthesized using a palladium catalysed Mizoroki-Heck reaction. This methodology tolerates various functional groups and gives the corresponding products in yields between 14 and 99%, which were strongly dependent on the electronic character of the aryl halides.
Article
A novel selective catalytic reduction method of tertiary phosphine oxides to the corresponding phosphines has been developed. Notably, the reaction proceeds smoothly with low catalyst loadings of 1-5mol% even at low temperature (70°C). Under the optimized conditions various phosphine oxides could be selectively reduced and the desired phosphines we...
Article
Full-text available
The palladium‐catalyzed CH activation and arylation of N‐methylpyrrole and N‐phenylpyrrole allowed a convenient synthesis of diarylpyrroles. The reactions were performed by using tetrabutylammonium acetate as an ionic solvent, which allowed for the application of a ligand‐free catalytic system by using simple palladium salts or polyvinylpyrrolidone...

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