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 borons 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.
- Scott N. Mlynarski, Christopher H. Schuster, James P. Morken. Asymmetric synthesis from terminal alkenes by cascades of diboration and cross-coupling. Nature, 2013; DOI: 10.1038/nature12781
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