Decarbonylative organoboron cross-coupling of esters by nickel catalysis

Kei Muto, Junichiro Yamaguchi, Djamaladdin G. Musaev, Kenichiro Itami

Research output: Contribution to journalArticle

126 Citations (Scopus)

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 a € estera € cross-coupling should find significant use in synthetic chemistry as an alternative to the standard halide-based Suzuki-Miyaura coupling.

Original languageEnglish
Article number7508
JournalNature Communications
Volume6
DOIs
Publication statusPublished - 2015 Jun 29
Externally publishedYes

Fingerprint

cross coupling
Nickel
Catalysis
catalysis
esters
Esters
nickel
halides
Boronic Acids
chemistry
Agrochemicals
Nucleophiles
Molecules
Boron
nucleophiles
organic materials
Carboxylic Acids
carboxylic acids
molecules
boron

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)
  • Physics and Astronomy(all)

Cite this

Decarbonylative organoboron cross-coupling of esters by nickel catalysis. / Muto, Kei; Yamaguchi, Junichiro; Musaev, Djamaladdin G.; Itami, Kenichiro.

In: Nature Communications, Vol. 6, 7508, 29.06.2015.

Research output: Contribution to journalArticle

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