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XBCBCAT SIGNED

From Supramolecular Chemistry to Organocatalysis: Fundamental Studies on the Use of Little-Explored Non-Covalent Interactions in Organic Synthesis

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EC-Contrib. €

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Project "XBCBCAT" data sheet

The following table provides information about the project.

Coordinator
RUHR-UNIVERSITAET BOCHUM 

Organization address
address: UNIVERSITAETSSTRASSE 150
city: BOCHUM
postcode: 44801
website: www.rub.de

contact info
title: n.a.
name: n.a.
surname: n.a.
function: n.a.
email: n.a.
telephone: n.a.
fax: n.a.

 Coordinator Country Germany [DE]
 Project website http://www.ruhr-uni-bochum.de/oc1/huber/research/topics.html
 Total cost 1˙497˙916 €
 EC max contribution 1˙497˙916 € (100%)
 Programme 1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC))
 Code Call ERC-2014-STG
 Funding Scheme ERC-STG
 Starting year 2015
 Duration (year-month-day) from 2015-05-01   to  2020-04-30

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    RUHR-UNIVERSITAET BOCHUM DE (BOCHUM) coordinator 1˙497˙916.00

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 Project objective

Hydrogen-bonds have found widespread use in various fields of chemistry, including supramolecular chemistry, organic chemistry, and more lately organocatalysis. Although a multitude of structurally different hydrogen-bond donors has been developed, their mode of action is in all cases necessarily based on the same interacting atom, hydrogen.

In this proposal, we aim to develop first applications for two, previously very little explored non-covalent interactions that are based on electrophilic halogen or chalcogen substituents (“halogen-bonds” and “chalcogen bonds”).

The first objective is to open the way for the use of chiral multidentate halogen-bond donors (i.e., halogen-based Lewis acids) for enantiodiscrimination. After the synthesis of suitable candidate compounds, we will apply them in the following research areas: a) the resolution of racemic mixtures by co-crystallization with chiral halogen-bond donors, and b) the use of these Lewis acids in enantioselective organocatalysis.

Within the second objective, we will strive to establish first-of-its-kind applications of chalcogen-based Lewis acids in organic synthesis and organocatalysis. In contrast to halogen-bonds, chalcogen-bonds feature two substituents on the interacting atom as well as two electrophilic axes. In the first phase of this aim, we will synthesize neutral and cationic, mono- and bidentate candidate compounds and determine their association constants with a variety of Lewis bases. Based on this date, we subsequently seek to use these novel Lewis acids as activators or catalysts in organic transformations.

We anticipate that the realization of these applications, all of which are unprecedented, will be a crucial first step towards establishing further non-covalent interactions as useful tools in chiral recognition and chemical synthesis. In the long-term, we foresee these little-explored interactions becoming powerful complements to the ubiquitous hydrogen-bonds.

 Publications

year authors and title journal last update
List of publications.
2019 P. Wonner, T. Steinke, S. M. Huber
Activation of Quinolines by Cationic Chalcogen Bond Donors
published pages: 1673-1678, ISSN: 0936-5214, DOI: 10.1055/s-0039-1690110
Synlett 30/14 2019-12-16
2019 Alexander Dreger, Patrick Wonner, Elric Engelage, Sebastian M. Walter, Raphael Stoll, Stefan M. Huber
A halogen-bonding-catalysed Nazarov cyclisation reaction
published pages: 8262-8265, ISSN: 1359-7345, DOI: 10.1039/c9cc02816a
Chemical Communications 55/57 2019-12-16
2017 Patrick Wonner, Lukas Vogel, Florian Kniep, Stefan M. Huber
Catalytic Carbon-Chlorine Bond Activation by Selenium-Based Chalcogen Bond Donors
published pages: 16972-16975, ISSN: 0947-6539, DOI: 10.1002/chem.201704502
Chemistry - A European Journal 23/67 2019-05-29
2017 Patrick Wonner, Lukas Vogel, Maximilian Düser, Luís Gomes, Florian Kniep, Bert Mallick, Daniel B. Werz, Stefan M. Huber
Carbon-Halogen Bond Activation by Selenium-Based Chalcogen Bonding
published pages: 12009-12012, ISSN: 1433-7851, DOI: 10.1002/anie.201704816
Angewandte Chemie International Edition 56/39 2019-05-29
2017 Jan-Philipp Gliese, Stefan H. Jungbauer, Stefan M. Huber
A halogen-bonding-catalyzed Michael addition reaction
published pages: 12052-12055, ISSN: 1359-7345, DOI: 10.1039/C7CC07175B
Chemical Communications 53/88 2019-05-29

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