Featured Research

from universities, journals, and other organizations

A bit of boron, a pinch of palladium: One-stop shop for the Suzuki reaction

Date:
August 2, 2011
Source:
Ludwig-Maximilians-Universitaet Muenchen (LMU)
Summary:
Thanks to chemists in Munich, a crucial type of intermediate in the so-called Suzuki reaction can now be synthesized using an economical "one-pot" strategy. These compounds are used on an industrial scale to make the carbon scaffolds that form the basis of useful drugs and innovative materials.

Thanks to a team of chemists from Ludwig-Maximilians-Universitaet (LMU) in Munich, a crucial type of intermediate in the so-called Suzuki reaction can now be synthesized using an economical “one-pot” strategy. These compounds are used on an industrial scale to make the carbon scaffolds that form the basis of useful drugs and innovative materials.

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."

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 Sδmann, 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."


Story Source:

The above story is based on materials provided by Ludwig-Maximilians-Universitaet Muenchen (LMU). Note: Materials may be edited for content and length.


Journal Reference:

  1. Benjamin A. Haag, Christoph Sδmann, Anukul Jana, Paul Knochel. Practical One-Pot Preparation of Magnesium Di(hetero)aryl- and Magnesium Dialkenylboronates for Suzuki-Miyaura Cross-Coupling Reactions. Angewandte Chemie International Edition, 2011; 50 (32): 7290 DOI: 10.1002/anie.201103022

Cite This Page:

Ludwig-Maximilians-Universitaet Muenchen (LMU). "A bit of boron, a pinch of palladium: One-stop shop for the Suzuki reaction." ScienceDaily. ScienceDaily, 2 August 2011. <www.sciencedaily.com/releases/2011/08/110801114123.htm>.
Ludwig-Maximilians-Universitaet Muenchen (LMU). (2011, August 2). A bit of boron, a pinch of palladium: One-stop shop for the Suzuki reaction. ScienceDaily. Retrieved April 24, 2014 from www.sciencedaily.com/releases/2011/08/110801114123.htm
Ludwig-Maximilians-Universitaet Muenchen (LMU). "A bit of boron, a pinch of palladium: One-stop shop for the Suzuki reaction." ScienceDaily. www.sciencedaily.com/releases/2011/08/110801114123.htm (accessed April 24, 2014).

Share This



More Matter & Energy News

Thursday, April 24, 2014

Featured Research

from universities, journals, and other organizations


Featured Videos

from AP, Reuters, AFP, and other news services

UN Joint Mission Starts Removing Landmines in Cyprus

UN Joint Mission Starts Removing Landmines in Cyprus

AFP (Apr. 23, 2014) — The UN mission in Cyprus (UNFICYP) led a mine clearance demonstration on Wednesday in the UN-controlled buffer zone where demining operations are being conducted near the Cypriot village of Mammari. Duration: 01:00 Video provided by AFP
Powered by NewsLook.com
Air Force: $4.2B Saved from Grounding A-10s

Air Force: $4.2B Saved from Grounding A-10s

AP (Apr. 23, 2014) — Speaking about the future of the United States Air Force, Chief of Staff Gen. Mark Welsh says the choice to divest the A-10 fleet was logical and least impactful. (April 23) Video provided by AP
Powered by NewsLook.com
Jets Fuel Jump in Boeing's Revenue

Jets Fuel Jump in Boeing's Revenue

Reuters - Business Video Online (Apr. 23, 2014) — A sharp rise in revenue for commercial jets offset a decline in Boeing's defense business. And a big increase in deliveries lifted profitability. Fred Katayama reports. Video provided by Reuters
Powered by NewsLook.com
Is North Korea Planning Nuclear Test #4?

Is North Korea Planning Nuclear Test #4?

Newsy (Apr. 22, 2014) — South Korean officials say North Korea is preparing to conduct another nuclear test, but is Pyongyang just bluffing this time? Video provided by Newsy
Powered by NewsLook.com

Search ScienceDaily

Number of stories in archives: 140,361

Find with keyword(s):
 
Enter a keyword or phrase to search ScienceDaily for related topics and research stories.

Save/Print:
Share:  

Breaking News:
from the past week

In Other News

... from NewsDaily.com

Science News

Health News

Environment News

Technology News



Save/Print:
Share:  

Free Subscriptions


Get the latest science news with ScienceDaily's free email newsletters, updated daily and weekly. Or view hourly updated newsfeeds in your RSS reader:

Get Social & Mobile


Keep up to date with the latest news from ScienceDaily via social networks and mobile apps:

Have Feedback?


Tell us what you think of ScienceDaily -- we welcome both positive and negative comments. Have any problems using the site? Questions?
Mobile iPhone Android Web
Follow Facebook Twitter Google+
Subscribe RSS Feeds Email Newsletters
Latest Headlines Health & Medicine Mind & Brain Space & Time Matter & Energy Computers & Math Plants & Animals Earth & Climate Fossils & Ruins