Aromatic Esters and Boronic Acids Used with Nickel Catalyst to Greatly Expand Number of Substrates for Powerful Suzuki-Miyaura Cross-Coupling Reaction; “Beautiful Work in the Frontier of Organic Transformations”

Making carbon-carbon bonds continues to be an important strategy to synthesize useful pharmaceuticals, agrochemicals, and organic materials. Through the global collaboration between WPI-ITbM and NSF-CCHF, chemists have expanded the scope of a Nobel Prize-winning carbon-carbon bond forming reaction by using aromatic esters and boronic acids as coupling partners in the presence of an economically and environmentally friendly nickel catalyst. Esters have been identified to act as a new and clean coupling partner for the carbon-carbon bond forming cross-coupling reaction to make useful compounds for pharmaceuticals, agrochemicals and organic materials. In a new collaborative study published online on June 29, 2015 in an open-access article in Nature Communications, synthetic and theoretical chemists at the Institute of Transformative Bio-Molecules (ITbM), Nagoya University in Japan and the NSF Center for Selective C-H Functionalization (NSF-CCHF) at Emory University in the United States have shown that a relatively inexpensive nickel catalyst triggers the decarbonylative cross-coupling between aromatic esters and boronic acids. The article is titled “Decarbonylative Organoboron Cross-Coupling of Esters by Nickel Catalysis.” The cross-coupling reaction, known as the Suzuki-Miyaura cross-coupling reaction is an extremely powerful strategy to synthesize a variety of significant organic compounds on an industrial scale, thus leading to the Nobel Prize in Chemistry in 2010. The Suzuki-Miyaura cross-coupling reaction is usually catalyzed by a palladium catalyst to couple boronic acids with organic halides. However, while this reaction is very powerful, these reaction partners can generate corrosive waste byproducts. Hence, many groups have been working to develop alternative coupling partners.
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