Featured Research

from universities, journals, and other organizations

Chemical synthesis: A simple technique for highly functionalized compounds

Date:
September 25, 2013
Source:
Organization of Frontier Science and Innovation, Kanazawa University
Summary:
Researchers have demonstrated a technique that allows direct functionalization of alkenes without the need for metallic reagents, photolysis or extreme reaction conditions.

Oxidative nitration of alkene 1a to produce ɣ-lactol (2a) and nitrate ester (3a).
Credit: Image courtesy of Organization of Frontier Science and Innovation, Kanazawa University

Researchers at Kanazawa University have demonstrated a technique that allows direct functionalization of alkenes without the need for metallic reagents, photolysis or extreme reaction conditions.

Related Articles


The addition of functional groups to certain unsaturated hydrocarbons, known as alkenes, is a crucial stage in the synthesis of various compounds, including many plastics.

For these functionalization reactions to occur a carbon-hydrogen (C-H) bond must be activated, which is traditionally achieved using transition metal catalysts. However use of these catalysts has both economical and environmental drawbacks. Now researchers at Kanazawa University have demonstrated a technique that allows direct functionalization of alkenes without the need for metallic reagents, photolysis or extreme reaction conditions.

Tsuyoshi Taniguchi and colleagues at Kanazawa University developed work where they had reported a reaction of alkenes using tert-butyl nitrite and molecular oxygen. They monitored the reaction products -- ɣ-lactol and nitrate ester -- using different solvents, and found that a high polarity aprotic (hydrogen-free) solvent gave the best yield, with ɣ-lactol as the major product.

They then experimented with different alkenes and observed how the products differed for branched and linear alkenes. Further reduction reactions demonstrated how the new synthesis technique could yield a range of useful derivatives, producing highly functionalized compounds from simple alkenes in only one or two steps.

The researchers were also able to propose a possible reaction mechanism. While the exact pathway remains uncertain, they suggest that the key step is the cleavage of an oxygen-oxygen bond to form a highly reactive alkoxy radical -- a molecular component comprising an oxygen with single bonds either side to hydrocarbon chains.

The work demonstrates how substantial yields of highly functionalized compounds can be achieved from simple organic molecules in simple conditions with no metal catalyst. The authors conclude, "We believe that such 'simple and advanced reactions' are promising in the development of useful synthetic methods involving direct C-H functionalization."


Story Source:

The above story is based on materials provided by Organization of Frontier Science and Innovation, Kanazawa University. Note: Materials may be edited for content and length.


Journal Reference:

  1. Tsuyoshi Taniguchi, Yuki Sugiura, Takashi Hatta, Atsushi Yajima, Hiroyuki Ishibashi. Multifunctionalization of alkenes via aerobic oxynitration and sp3 C–H oxidation. Chemical Communications, 2013; 49 (22): 2198 DOI: 10.1039/C3CC00130J

Cite This Page:

Organization of Frontier Science and Innovation, Kanazawa University. "Chemical synthesis: A simple technique for highly functionalized compounds." ScienceDaily. ScienceDaily, 25 September 2013. <www.sciencedaily.com/releases/2013/09/130925112231.htm>.
Organization of Frontier Science and Innovation, Kanazawa University. (2013, September 25). Chemical synthesis: A simple technique for highly functionalized compounds. ScienceDaily. Retrieved October 24, 2014 from www.sciencedaily.com/releases/2013/09/130925112231.htm
Organization of Frontier Science and Innovation, Kanazawa University. "Chemical synthesis: A simple technique for highly functionalized compounds." ScienceDaily. www.sciencedaily.com/releases/2013/09/130925112231.htm (accessed October 24, 2014).

Share This



More Matter & Energy News

Friday, October 24, 2014

Featured Research

from universities, journals, and other organizations


Featured Videos

from AP, Reuters, AFP, and other news services

IKEA Desk Converts From Standing to Sitting With One Button

IKEA Desk Converts From Standing to Sitting With One Button

Buzz60 (Oct. 24, 2014) IKEA is out with a new convertible desk that can convert from a sitting desk to a standing one with just the push of a button. Jen Markham explains. Video provided by Buzz60
Powered by NewsLook.com
Ebola Protective Suits Being Made in China

Ebola Protective Suits Being Made in China

AFP (Oct. 24, 2014) A factory in China is busy making Ebola protective suits for healthcare workers and others fighting the spread of the virus. Duration: 00:38 Video provided by AFP
Powered by NewsLook.com
Real-Life Transformer Robot Walks, Then Folds Into a Car

Real-Life Transformer Robot Walks, Then Folds Into a Car

Buzz60 (Oct. 24, 2014) Brave Robotics and Asratec teamed with original Transformers toy company Tomy to create a functional 5-foot-tall humanoid robot that can march and fold itself into a 3-foot-long sports car. Jen Markham has the story. Video provided by Buzz60
Powered by NewsLook.com
Police Testing New Gunfire Tracking Technology

Police Testing New Gunfire Tracking Technology

AP (Oct. 24, 2014) A California-based startup has designed new law enforcement technology that aims to automatically alert dispatch when an officer's gun is unholstered and fired. Two law enforcement agencies are currently testing the technology. (Oct. 24) Video provided by AP
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:

Strange & Offbeat Stories


Space & Time

Matter & Energy

Computers & Math

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