Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

Arylboronates made easy

20.08.2015

Abandoning expensive and toxic materials in chemical synthesis: This is the goal pursued by scientists at the University of Würzburg. In the magazine "Angewandte Chemie", they describe a new way to achieve this goal, a surprise included.

Arylboronates are important base materials for the industrial fabrication of countless products, including pharmaceutical drugs, chemicals for agriculture or liquid crystals for displays. The synthesis of arylboronates to date has required metalliferous catalysts such as palladium, iridium or nickel.


Using zinc as catalyst, circular molecules can be fitted with two boronate groups at the same time.

(Picture: Todd Marder)

These materials have a number of drawbacks: The metals are either expensive, toxic or both. Nickel, for example, can trigger allergies. When used in pharmaceutical drug production, the nickel has to be removed again after the reaction in a complex process.

Progress with zinc catalysts

The Würzburg chemists Shubhankar Kumar Bose and Todd Marder now present an entirely new catalytic process that enables arylboronates to be produced at lower costs and with less environmental impact. Their success is based on the use of zinc catalysts. "Zinc is cheap, non-toxic and abundant on our planet," Marder names some of the metal's benefits.

As the team reports in "Angewandte Chemie", a baffling effect occurred during their research work. The scientists haven't been able to fully account for the effect yet, but it should cause a stir among experts, because it might deliver the key to facilitating the synthesis of many important arylboronates in the future.

Simultaneous bonding of boronate groups

What caused the astonishment? To produce the arylboronates, circular molecules are used in which either a hydrogen atom or a halogen atom (bromine, fluorine or iodine) is replaced with a so-called boronate group. When the Würzburg scientists initiated this exchange using their zinc catalyst, the two actions happened simultaneously: Both the halogen atom and an adjacent hydrogen atom were replaced by boronate. The result is an aryl with two boronate groups. Usually, these molecules are not so easy to synthesise and they are highly interesting for industrial synthesis.

"This was totally unexpected," says Marder, "and we don't know yet which chemical mechanism caused the phenomenon." The chemists already conducted a number of experiments to exclude some reaction channels. Following a process of elimination they hence suggest one possible reaction mechanism in "Angewandte Chemie".

Next steps in research

In a next step, the scientists want to find out what happened exactly during the reaction with the zinc catalyst. And they are working on increasing the yield of the much sought after substance: The reaction produces around 70 percent of molecules with one boronate group and 30 percent with two boronate groups.

Evolution in catalysis

This success is the preliminary climax of an "evolution of the catalysis" in which Marder's team has played a leading role in the past years. In 1995, the catalysed aryl borylation was successfully conducted in Japan for the first time using palladium; the corresponding reaction is named Miyaura borylation after its inventor.

Arylboronates are needed for the Suzuki-Miyaura reaction. In 2010, Akira Suzuki was awarded the Nobel Prize in Chemistry for its successful implementation. In 2009, Marder's team triggered such reactions using copper catalysts at the University of Durham in England back then. Copper is a low-priced transition metal with low toxicity.

Shubhankar Kumar Bose, who joined the University of Würzburg as a Humboldt scholar in 2013, finally had the idea to try zinc as a catalyst. In 2014, the reaction succeeded first with chain-like molecules (alkylboronates) and now also with circular boronates. Their discovery has another advantage: Zinc is even cheaper than copper and non-toxic.

"Zinc-Catalyzed Dual C–X and C–H Borylation of Aryl Halides“,Shubhankar Kumar Bose, Andrea Deißenberger, Antonius Eichhorn, Patrick G. Steel, Zhenyang Lin, Todd B. Marder. Angewandte Chemie International Edition, published online 18 August 2015, DOI: 10.1002/anie.201505603

Contact

Prof. Dr. Todd Marder, Institute of Inorganic Chemistry, University of Würzburg, Phone +49 931 31-85514, todd.marder@uni-wuerzburg.de

Robert Emmerich | Julius-Maximilians-Universität Würzburg
Further information:
http://www.uni-wuerzburg.de

More articles from Life Sciences:

nachricht Ion treatments for cardiac arrhythmia — Non-invasive alternative to catheter-based surgery
20.01.2017 | GSI Helmholtzzentrum für Schwerionenforschung GmbH

nachricht Seeking structure with metagenome sequences
20.01.2017 | DOE/Joint Genome Institute

All articles from Life Sciences >>>

The most recent press releases about innovation >>>

Die letzten 5 Focus-News des innovations-reports im Überblick:

Im Focus: Traffic jam in empty space

New success for Konstanz physicists in studying the quantum vacuum

An important step towards a completely new experimental access to quantum physics has been made at University of Konstanz. The team of scientists headed by...

Im Focus: How gut bacteria can make us ill

HZI researchers decipher infection mechanisms of Yersinia and immune responses of the host

Yersiniae cause severe intestinal infections. Studies using Yersinia pseudotuberculosis as a model organism aim to elucidate the infection mechanisms of these...

Im Focus: Interfacial Superconductivity: Magnetic and superconducting order revealed simultaneously

Researchers from the University of Hamburg in Germany, in collaboration with colleagues from the University of Aarhus in Denmark, have synthesized a new superconducting material by growing a few layers of an antiferromagnetic transition-metal chalcogenide on a bismuth-based topological insulator, both being non-superconducting materials.

While superconductivity and magnetism are generally believed to be mutually exclusive, surprisingly, in this new material, superconducting correlations...

Im Focus: Studying fundamental particles in materials

Laser-driving of semimetals allows creating novel quasiparticle states within condensed matter systems and switching between different states on ultrafast time scales

Studying properties of fundamental particles in condensed matter systems is a promising approach to quantum field theory. Quasiparticles offer the opportunity...

Im Focus: Designing Architecture with Solar Building Envelopes

Among the general public, solar thermal energy is currently associated with dark blue, rectangular collectors on building roofs. Technologies are needed for aesthetically high quality architecture which offer the architect more room for manoeuvre when it comes to low- and plus-energy buildings. With the “ArKol” project, researchers at Fraunhofer ISE together with partners are currently developing two façade collectors for solar thermal energy generation, which permit a high degree of design flexibility: a strip collector for opaque façade sections and a solar thermal blind for transparent sections. The current state of the two developments will be presented at the BAU 2017 trade fair.

As part of the “ArKol – development of architecturally highly integrated façade collectors with heat pipes” project, Fraunhofer ISE together with its partners...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

Event News

Sustainable Water use in Agriculture in Eastern Europe and Central Asia

19.01.2017 | Event News

12V, 48V, high-voltage – trends in E/E automotive architecture

10.01.2017 | Event News

2nd Conference on Non-Textual Information on 10 and 11 May 2017 in Hannover

09.01.2017 | Event News

 
Latest News

Helmholtz International Fellow Award for Sarah Amalia Teichmann

20.01.2017 | Awards Funding

An innovative high-performance material: biofibers made from green lacewing silk

20.01.2017 | Materials Sciences

Ion treatments for cardiac arrhythmia — Non-invasive alternative to catheter-based surgery

20.01.2017 | Life Sciences

VideoLinks
B2B-VideoLinks
More VideoLinks >>>