A chemistry collaboration has led to a way to incorporate carbon dioxide into a series of organic molecules that are vital to pharmaceutical development.
The research team came up with an innovative idea. They could make two different products by changing the type of reactor.
The paper was published in January in Nature. The paper's co-lead authors are two graduate students and a professor at a Chinese university.
The Cornell team, led by Song Lin, professor of chemistry and chemical biology in the College of Arts and Sciences, has previously used the process of electrochemistry to stitch together simple carbon molecule and form complex compounds without the need for precious metals or other catalysts.
pyridine is the second most prevalent Heterocycle in FDA approved drugs. Heterocyles are organic compounds in which the molecule's atoms are linked into ring structures The structural units are referred to as "pharmacophores" for their presence in active compounds. They are found in many different types of chemicals.
The researchers wanted to make pyridines with carbon dioxide added to them. The advantage of introducing carbon dioxide to a pyridine ring is that it can change the function of a molecule by binding to certain targets. The two molecule are not compatible. Pyridine is a molecule that reacts with something.
The paper's co-senior author, Lin, said there were few ways to introduce carbon dioxide to apyridine. The current methods don't work very well.
Lin's lab was able to create carboxylated pyridines with the help of Yu's group, which specialized in using carbon dioxide in organic synthesis.
Lin said that chemistry gives you the ability to dial in the potential that is enough to make a molecule work. That is how we achieved this reaction.
The team's discovery came while they were doing the experiment. Chemists can run an electrochemical reaction in one of two ways: in an undivided cell in which the anode and cathode are in the same solution, or in a divided cell where the anode and cathode are separated by a porous divider. One approach is more efficient than the other.
Lin's group found that if they switched from a divided cell to an undivided one they could attach the carbon dioxide molecule on different positions of the pyridine ring.
Lin said that this is the first time they have found that by simply changing the cell, you can completely change the product. I think that mechanistic understanding of why it happened will allow us to apply the same strategy to other molecule, not just pyridines, and maybe make other molecule in this controlled fashion. That principle can be generalized to other systems.
The project's form of carbon dioxide utilization is not going to solve the global challenge of climate change, but it is a small step towards using excessive carbon dioxide in a useful way.
The co- authors were Yi Wang and Zhipeng Lu.
The site selectivity in N-heteroarene carboxylations is dictated by the electrical reactor. It's 10.1038
Journal information: Nature
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