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.

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 September 19, 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 September 19, 2014).

Share This



More Matter & Energy News

Friday, September 19, 2014

Featured Research

from universities, journals, and other organizations


Featured Videos

from AP, Reuters, AFP, and other news services

Virtual Reality Headsets Unveiled at Tokyo Game Show

Virtual Reality Headsets Unveiled at Tokyo Game Show

AFP (Sep. 18, 2014) Several companies unveiled virtual reality headsets at the Tokyo Game Show, Asia's largest digital entertainment exhibition. Duration: 00:48 Video provided by AFP
Powered by NewsLook.com
Apple's iOS8 Includes New 'Killswitch' To Curb Theft

Apple's iOS8 Includes New 'Killswitch' To Curb Theft

Newsy (Sep. 18, 2014) Apple's new operating system, iOS 8, comes with Apple's killswitch feature already activated, unlike all the models before it. Video provided by Newsy
Powered by NewsLook.com
Stocks Hit All-Time High as Fed Holds Steady

Stocks Hit All-Time High as Fed Holds Steady

AP (Sep. 17, 2014) The Federal Reserve signaled Wednesday that it plans to keep a key interest rate at a record low because a broad range of U.S. economic measures remain subpar. Stocks hit an all-time high on the news. (Sept. 17) Video provided by AP
Powered by NewsLook.com
Space Race Pits Bezos Vs Musk

Space Race Pits Bezos Vs Musk

Reuters - Business Video Online (Sep. 16, 2014) Amazon CEO Jeff Bezos' startup will team up with Boeing and Lockheed to develop rocket engines as Elon Musk races to have his rockets certified. Fred Katayama reports. Video provided by Reuters
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