Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

A bit of boron, a pinch of palladium

02.08.2011
One-stop shop for the Suzuki reaction

Carbon-containing compounds are at the heart of organic chemistry, and carbon is the basis of all living matter. However, the so-called Suzuki reaction provides a simple means of creating carbon-carbon bonds to form compounds that can serve as the starting points for the synthesis of an infinite variety of organic molecules.

A team of researchers led by LMU chemist Professor Paul Knochel has recently developed a practical and general method for the synthesis of a class of intermediates that readily undergo the Suzuki reaction. “The new method is broadly applicable to diverse starting compounds and is very economical because it produces very few unwanted byproducts,” says Knochel. “It should also be of great interest in an industrial setting, where Suzuki reactions are used in the development of medicinal compounds and novel materials such as liquid crystals for display screens.” (Angewandte Chemie International Edition, 1. August 2011)

The Suzuki reaction – which involves the use of palladium to catalyze the cross-coupling of organoboron compounds with organic halogen-containing molecules – makes it possible to link carbon atoms together in a very straightforward way. The products of the reaction can then be utilized for the construction of a virtually unlimited number of organic substances. The Suzuki reaction thus forms the basis for the synthesis of novel drugs and innovative materials. Akira Suzuki was awarded the Nobel Prize in Chemistry for his discovery of the reaction that bears his name.

Knochel and his team were hoping to extend the applicability of the reaction by finding an easy, economical and general way to synthesize the necessary organoboron compounds so that they could be used in Suzuki reactions without further purification. “We were able to optimize the process in such a way that the boronates can be made in a one-pot reaction”, says Christoph Sämann, who made a major contribution to the study. “The method works well under very mild conditions, is compatible with many different functional groups and can therefore be applied to a wide range of compounds.”

In contrast to the organoboronates that have been used so far, the products generated via the new synthetic route have two organic groups attached to the boron atom, and both can be transferred, without loss, in the course of the subsequent Suzuki reaction. “This significantly improves overall yields, making the reaction much more economical,” says Knochel. “The new reaction also produces less waste, which is an especially important consideration in industrial applications.” (suwe)

Publication:
Practical One-pot Preparation of Magnesium Diaryl-, Diheteroaryl- and Dialkenyl-boronates for Suzuki-Miyaura Cross-Couplings
Benjamin A. Haag, Christoph Sämann, Anukul Jana, Paul Knochel;
Angewandte Chemie, International Edition, 1. August 2011;
Web: http://dx.doi.org/10.1002/anie.201103022
Contact:
Professor Dr. Paul Knochel
Department of Chemistry and Biochemistry, LMU Munich
Phone: +49 89 / 2180 – 77681
Fax: +49 89 / 2180 – 77680
Email: knoch@cup.uni-muenchen.de

Kathrin Bilgeri | EurekAlert!
Further information:
http://www.knochel.cup.uni-muenchen.de
http://www.lmu.de

More articles from Life Sciences:

nachricht Symbiotic bacteria: from hitchhiker to beetle bodyguard
28.04.2017 | Johannes Gutenberg-Universität Mainz

nachricht Nose2Brain – Better Therapy for Multiple Sclerosis
28.04.2017 | Fraunhofer-Institut für Grenzflächen- und Bioverfahrenstechnik IGB

All articles from Life Sciences >>>

The most recent press releases about innovation >>>

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

Im Focus: Making lightweight construction suitable for series production

More and more automobile companies are focusing on body parts made of carbon fiber reinforced plastics (CFRP). However, manufacturing and repair costs must be further reduced in order to make CFRP more economical in use. Together with the Volkswagen AG and five other partners in the project HolQueSt 3D, the Laser Zentrum Hannover e.V. (LZH) has developed laser processes for the automatic trimming, drilling and repair of three-dimensional components.

Automated manufacturing processes are the basis for ultimately establishing the series production of CFRP components. In the project HolQueSt 3D, the LZH has...

Im Focus: Wonder material? Novel nanotube structure strengthens thin films for flexible electronics

Reflecting the structure of composites found in nature and the ancient world, researchers at the University of Illinois at Urbana-Champaign have synthesized thin carbon nanotube (CNT) textiles that exhibit both high electrical conductivity and a level of toughness that is about fifty times higher than copper films, currently used in electronics.

"The structural robustness of thin metal films has significant importance for the reliable operation of smart skin and flexible electronics including...

Im Focus: Deep inside Galaxy M87

The nearby, giant radio galaxy M87 hosts a supermassive black hole (BH) and is well-known for its bright jet dominating the spectrum over ten orders of magnitude in frequency. Due to its proximity, jet prominence, and the large black hole mass, M87 is the best laboratory for investigating the formation, acceleration, and collimation of relativistic jets. A research team led by Silke Britzen from the Max Planck Institute for Radio Astronomy in Bonn, Germany, has found strong indication for turbulent processes connecting the accretion disk and the jet of that galaxy providing insights into the longstanding problem of the origin of astrophysical jets.

Supermassive black holes form some of the most enigmatic phenomena in astrophysics. Their enormous energy output is supposed to be generated by the...

Im Focus: A Quantum Low Pass for Photons

Physicists in Garching observe novel quantum effect that limits the number of emitted photons.

The probability to find a certain number of photons inside a laser pulse usually corresponds to a classical distribution of independent events, the so-called...

Im Focus: Microprocessors based on a layer of just three atoms

Microprocessors based on atomically thin materials hold the promise of the evolution of traditional processors as well as new applications in the field of flexible electronics. Now, a TU Wien research team led by Thomas Müller has made a breakthrough in this field as part of an ongoing research project.

Two-dimensional materials, or 2D materials for short, are extremely versatile, although – or often more precisely because – they are made up of just one or a...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

Event News

Fighting drug resistant tuberculosis – InfectoGnostics meets MYCO-NET² partners in Peru

28.04.2017 | Event News

Expert meeting “Health Business Connect” will connect international medical technology companies

20.04.2017 | Event News

Wenn der Computer das Gehirn austrickst

18.04.2017 | Event News

 
Latest News

Wireless power can drive tiny electronic devices in the GI tract

28.04.2017 | Medical Engineering

Ice cave in Transylvania yields window into region's past

28.04.2017 | Earth Sciences

Nose2Brain – Better Therapy for Multiple Sclerosis

28.04.2017 | Life Sciences

VideoLinks
B2B-VideoLinks
More VideoLinks >>>