title: Decarbonylative organoboron cross-coupling of esters by nickel catalysis.
abstract: The Suzuki-Miyaura cross-coupling is a metal-catalysed reaction in which boron-based nucleophiles and halide-based electrophiles are reacted to form a single molecule. This is one of the most reliable tools in synthetic chemistry, and is extensively used in the synthesis of pharmaceuticals, agrochemicals and organic materials. Herein, we report a significant advance in the choice of electrophilic coupling partner in this reaction. With a user-friendly and inexpensive nickel catalyst, a range of phenyl esters of aromatic, heteroaromatic and aliphatic carboxylic acids react with boronic acids in a decarbonylative manner. Overall, phenyl ester moieties function as leaving groups. Theoretical calculations uncovered key mechanistic features of this unusual decarbonylative coupling. Since extraordinary numbers of ester-containing molecules are available both commercially and synthetically, this new 'ester' cross-coupling should find significant use in synthetic chemistry as an alternative to the standard halide-based Suzuki-Miyaura coupling.
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan.
authors.forename: Kei
authors.initials: K
authors.lastname: Muto
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan.
authors.forename: Junichiro
authors.initials: J
authors.lastname: Yamaguchi
authors.affiliation: Emory College's Research Center and Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, US.
authors.forename: Djamaladdin G
authors.initials: DG
authors.lastname: Musaev
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan.|JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya 464-8602, Japan.
authors.forename: Kenichiro
authors.initials: K
authors.lastname: Itami