Dual catalysts help synthesize alpha-olefins into new organic compounds

December 19, 2013

CHESTNUT HILL, MA (Dec. 19, 2013) - Boston College chemists have developed a new chemical synthesis methodology that converts chemicals known as alpha-olefins into new organic compounds. By combining a pair of catalytic reactions in sequence, the researchers converted inexpensive and plentiful chemicals into new boron-containing organic compounds prized by researchers.

The team reports in the current online edition of the journal Nature that their advance employed two catalytic reactions - one developed in their Boston College lab and another developed by colleagues at MIT. Combining the two reactions in a sequential process resulted in an unprecedented reaction that offered high levels of purity and selectivity, according to the lead researcher, Boston College Professor of Chemistry James P. Morken.

"We developed the first reaction to convert alpha-olefins into new boron compounds," said Morken. "The second reaction is a palladium-catalyzed reaction that uses a catalyst developed by a team at MIT. Together, these two reactions result in an unprecedented reaction process that works extremely well."

Organic chemists face the challenge of developing new compounds, such as medicines and materials, in a more efficient manner. A driving influence is to produce innovative compounds through simpler, more efficient processes that generate less waste and reduce costs, in particular through the use of readily available chemicals.

The team was surprised by the high level of reactivity in the boron-containing compounds from the first reaction, Morken said. The findings considerably expand the applications of alpha-olefins, a group of organic compounds distinguished by having a double bond at the primary, or alpha, position of their structure. While alpha-olefins are naturally occurring feedstocks that are usually converted into plastics, the increased reactivity that results from adding two boron atoms makes them suitable for wider range of research applications.

Morken said the new methodology should allow for the rapid and efficient production of important compounds from raw chemical feedstocks. As an example, the team used the new process to convert propene gas into phenethylamines, which are an important class of therapeutics, Morken said. In another application, the team used this new method of catalytic reactions to convert another alpha-olefin into pregabalin, which has been used in a variety of pain management drugs.

Morken conducted the research with doctoral students Scott Mlynarski and Chris Schuster, both co-authors of the Nature report.
-end-


Boston College

Related Organic Compounds Articles from Brightsurf:

Scientists discover new organic compounds that could have helped form the first cells
Chemists studying how life started often focus on biopolymers like peptides and nucleic acids, but modern biopolymers don't form easily without help from living organisms.

"Fireball" meteorite contains pristine extraterrestrial organic compounds
A fireball meteorite fell onto a frozen lake in Michigan, and since it was quickly collected before getting exposed to liquid water, it gives scientists a glimpse of what space rocks are like when they're still in space.

RUDN University chemist created a catalyst from orange peel for organic compounds production
N-heterocycles are organic substances used in the chemical industry and medicine.

Thawing permafrost releases organic compounds into the air
When permafrost thaws due to global warming, not only the greenhouse gases known to all, but also organic compounds are released from the soil.

Establishment of a rapid synthesis method for useful organic fluorine compounds
A new synthesis method has been developed for the efficient production of fluorinated alkenes.

Bioactive natural compounds for the fight against cancer
Phytoalexins are bioactive phytochemicals that have attracted much attention in recent years due to their health-promoting effects in humans and their vital role in plant health.

Novel bioaccumulative compounds found in marine bivalves
The present study screened known and unknown organohalogen compounds present in mussel and sediment samples from Hiroshima Bay.

New protocol for organic synthesis using organoboron compounds and visible-light
The generation of alkyl radicals was achieved by direct visible-light excitation of the organoborate complex, which was designed and synthesized from 'boracene,' which has a boron atom in the tetracene-like skeleton.

New algorithm predicts optimal materials among all possible compounds
Skoltech researchers have offered a solution to the problem of searching for materials with required properties among all possible combinations of chemical elements.

The discovery of new compounds for acting on the circadian clock
The research team comprised of Designated Associate Professor Tsuyoshi Hirota and Postdoctoral Fellows Simon Miller and Yoshiki Aikawa, of the Nagoya University Institute of Transformative Bio-Molecules, has succeeded in the discovery of novel compounds to lengthen the period of the circadian clock, and has shed light on their mechanisms of action.

Read More: Organic Compounds News and Organic Compounds Current Events
Brightsurf.com is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com.