A recent study published in Nature Communications stems from an international collaboration between scientists in Emory’s own NSF Center for Selective C-H Functionalization and the Institute of Transformative Bio-Molecules (ITbM) at Nayoga University, Japan. The article “Decarbonylative organoboron cross-coupling of esters by nickel catalysis” details work that expands the scope of a Nobel Prize-winning carbon-carbon bond reaction. The expanded reaction uses aromatic esters and boronic acids as coupling partners in the presence of a nickel catalyst. The nickel catalyst is economically and environmentally friendly, making it strategically useful for pharmaceutical, agro-chemical, and organic materials applications.
The new research builds on the 2010 Nobel prize-winning Suzuki-Miyaura cross-coupling reaction, an extremely powerful strategy to synthesize a variety of significant organic compounds on an industrial scale. The reaction is usually catalyzed by a pallidium catalyst to couple boronic acids with organic hallides. The result is extremely powerful but its reaction partners can generate corrosive waste byproducts.
Researchers at ITbM and CCHF have demonstrated that readily available esters–carbonyl compounds found in fat and oils–can be used as alternative coupling partners, generating useful products such as derivatives of plant metabolites and a drug for treating hypertension, telmisartan.
Esters are known for their distinctive odors, such as banana and pineapple, thus making them a popular ingredient in perfumes. Due to their high commercial and synthetic accessibility, the use of esters to couple with boronic acids greatly expands the scope of available substrates for the Suzuki-Miyaura cross-coupling reaction.
Theoretical calculations conducted by Professor Djamaladdin Musaev, Director of the Emerson Center at Emory University, contributed valuable insight to the mechanism of the decarbonylative cross-coupling reaction between aromatic esters and boronic acids.
“This is a beautiful work in the frontier of organic transformations,” said Musaev. “I am grateful to Professor Itami and the entire ITbM team for providing the opportunity for us to contribute to this novel research project.”
In turn, Professor Ken Itami of ITbM praises Musaev for elucidating the unusual decarbonylative cross-coupling reaction. “This is obviously a result of the strong collaboration between ITbM and CCHF. We will continue to work together to conduct further optimization of the reaction system to expand its scope.”
Itami and his colleagues envisage that ongoing advances in this reaction method may lead to the development of new industrial processes for making biologically and structurally active compounds, including aliphatic esters.