Decarbonylative organoboron cross-coupling of esters by nickel catalysis

Kei Muto, Junichiro Yamaguchi (), Djamaladdin G. Musaev () and Kenichiro Itami ()
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Kei Muto: Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University
Junichiro Yamaguchi: Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University
Djamaladdin G. Musaev: Emory University
Kenichiro Itami: Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University

Nature Communications, 2015, vol. 6, issue 1, 1-8

Abstract: 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.

Date: 2015
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DOI: 10.1038/ncomms8508

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