Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

Chemical synthesis: A simple technique for highly functionalized compounds

25.09.2013
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.

This research is also described in the inaugural June issue of the Kanazawa University Research Bulletin: http://www.kanazawa-u.ac.jp/research_bulletin/index.html


Oxidative nitration of alkene 1a to produce ɣ-lactol (2a) and nitrate ester (3a)

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.”

Further information

Organization of Frontier Science and Innovation
Kanazawa University
Kakuma, Kanazawa, Ishikawa 920-1192, Japan
E-mail: fsojimu@adm.kanazawa-u.ac.jp
Website: http://www.o-fsi.kanazawa-u.ac.jp/en/about/
About Kanazawa University
As the leading comprehensive university on the Sea of Japan coast, Kanazawa University has contributed greatly to higher education and academic research in Japan since it was founded in 1949. The University has three colleges and 16 schools offering courses in subjects that include medicine, computer engineering, and humanities.

The University is located on the coast of the Sea of Japan in Kanazawa—a city rich in history and culture. The city of Kanazawa has cultivated a highly respected intellectual profile since the time of the Kaga fiefdom (1598–1867). Kanazawa University is divided into two main campuses: Kakuma and Takaramachi for its approximately 12,200 students including 500 from overseas.

Journal information

Publication and Affiliation
Tsuyoshi Taniguchi,* Yuki Sugiura, Takashi Hatta, Atsushi Yajima and Hiroyuki Ishibashi Multifunctionalization of alkenes via aerobic oxynitration and sp3 C–H oxidation. Chem. Commun. 49 (2013) 2198-2200
* School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.

*corresponding author, e-mail address: tsuyoshi@p.kanazawa-u.ac.jp

Adarsh Sandhu | Research asia research news
Further information:
http://www.kanazawa-u.ac.jp
http://www.o-fsi.kanazawa-u.ac.jp/en/about/
http://www.researchsea.com

More articles from Life Sciences:

nachricht Researchers identify potentially druggable mutant p53 proteins that promote cancer growth
09.12.2016 | Cold Spring Harbor Laboratory

nachricht Plant-based substance boosts eyelash growth
09.12.2016 | Fraunhofer-Institut für Angewandte Polymerforschung IAP

All articles from Life Sciences >>>

The most recent press releases about innovation >>>

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

Im Focus: Electron highway inside crystal

Physicists of the University of Würzburg have made an astonishing discovery in a specific type of topological insulators. The effect is due to the structure of the materials used. The researchers have now published their work in the journal Science.

Topological insulators are currently the hot topic in physics according to the newspaper Neue Zürcher Zeitung. Only a few weeks ago, their importance was...

Im Focus: Significantly more productivity in USP lasers

In recent years, lasers with ultrashort pulses (USP) down to the femtosecond range have become established on an industrial scale. They could advance some applications with the much-lauded “cold ablation” – if that meant they would then achieve more throughput. A new generation of process engineering that will address this issue in particular will be discussed at the “4th UKP Workshop – Ultrafast Laser Technology” in April 2017.

Even back in the 1990s, scientists were comparing materials processing with nanosecond, picosecond and femtosesecond pulses. The result was surprising:...

Im Focus: Shape matters when light meets atom

Mapping the interaction of a single atom with a single photon may inform design of quantum devices

Have you ever wondered how you see the world? Vision is about photons of light, which are packets of energy, interacting with the atoms or molecules in what...

Im Focus: Novel silicon etching technique crafts 3-D gradient refractive index micro-optics

A multi-institutional research collaboration has created a novel approach for fabricating three-dimensional micro-optics through the shape-defined formation of porous silicon (PSi), with broad impacts in integrated optoelectronics, imaging, and photovoltaics.

Working with colleagues at Stanford and The Dow Chemical Company, researchers at the University of Illinois at Urbana-Champaign fabricated 3-D birefringent...

Im Focus: Quantum Particles Form Droplets

In experiments with magnetic atoms conducted at extremely low temperatures, scientists have demonstrated a unique phase of matter: The atoms form a new type of quantum liquid or quantum droplet state. These so called quantum droplets may preserve their form in absence of external confinement because of quantum effects. The joint team of experimental physicists from Innsbruck and theoretical physicists from Hannover report on their findings in the journal Physical Review X.

“Our Quantum droplets are in the gas phase but they still drop like a rock,” explains experimental physicist Francesca Ferlaino when talking about the...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

Event News

ICTM Conference 2017: Production technology for turbomachine manufacturing of the future

16.11.2016 | Event News

Innovation Day Laser Technology – Laser Additive Manufacturing

01.11.2016 | Event News

#IC2S2: When Social Science meets Computer Science - GESIS will host the IC2S2 conference 2017

14.10.2016 | Event News

 
Latest News

Researchers identify potentially druggable mutant p53 proteins that promote cancer growth

09.12.2016 | Life Sciences

Scientists produce a new roadmap for guiding development & conservation in the Amazon

09.12.2016 | Ecology, The Environment and Conservation

Satellites, airport visibility readings shed light on troops' exposure to air pollution

09.12.2016 | Health and Medicine

VideoLinks
B2B-VideoLinks
More VideoLinks >>>