Princeton researchers discover shortcut produce compounds

Princeton researchers discover shortcut to produce compounds

8:58 PM, 2nd December 2011
Princeton researchers discover shortcut to produce compounds
David MacMillan, professor of chemistry, Princeton University

NEW JERSEY, US: The researchers at Princeton University reported a technique to perform more than 1,000 chemical reactions a day with molecules never before combined. In a single day of trials, the Princeton researchers discovered a shortcut for producing pharmaceutical-like compounds that shaves weeks off the traditional process.

The basis of the research was to combine new technology with a unique, rapid-reaction approach that could allow chemists to explore unheard-of and potentially important chemical combinations without devoting years to the pursuit, explained David MacMillan, senior researcher and James S. McDonnell Professor of Chemistry, Princeton.

The MacMillan lab's technique developed a unique framework for creating new materials or finding better ways of producing existing ones, said Stephen Buchwald, professor of chemistry, Massachusetts Institute.

The team took molecules for which there was no obvious reaction between them and looked for 'accidental' reactivity. This approach could be useful for any field that requires new types of matter or a more efficient means of synthesizing known compounds.

The reaction involved a nitrogen-based molecule known as an amine that has hydrogen and carbon pair, and a circle of atoms stabilized by their bonds known as an aromatic ring.

The result was a carbon-nitrogen molecule with an aromatic ring, a building block of many amine-based pharmaceuticals, explained MacMillan. This class of drugs mimics natural amine molecules in the body and includes medications such as antihistamines, decongestants and antidepressants.

"We quickly realized that any pharmaceutical research chemist could immediately take these very simple components and, via a reaction no one had known about, start assembling molecules with an adjacent aromatic ring rapidly," said MacMillan.

"Instead of having to construct these important molecules circuitously using lots of different chemistry over a period of days if not weeks, we can now do it immediately in the space of one chemical reaction in one day."

"The way these types of molecules were produced in this project is highly efficient, and no person could truthfully say that they would have predicted this reaction," Buchwald said.

MacMillan and his team carried out photoredox catalysis on the molecules before each reaction cycle. Because the use of photoredox catalysts in organic-compound synthesis is relatively new — it has been typically used by chemists and in industry for processes such as energy storage and hydrogen production — it has not been as thoroughly explored as the more common method of using catalysts derived from metals such as nickel, gold and copper, MacMillan said. Thus, he said, elements with no history of reacting with each other could possibly produce results under this different approach.


© Princeton University News



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