Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents

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DOI

Herein, we report a nickel-catalyzed carbonylative coupling of α-bromonitriles and alkylzinc reagents with near stoichiometric carbon monoxide to give β-ketonitriles in good yields. The reaction is catalyzed by a readily available and stable nickel(II) pincer complex. The developed protocol tolerates substrates bearing a variety of functional groups, which would be problematic or incompatible with previous synthetic methods. Additionally, we demonstrate the suitability of the method for carbon isotope labeling by the synthesis of 13C-labeled β-ketonitriles and their transformation into isotopically labeled heterocycles.

Original languageEnglish
JournalChemistry - A European Journal
Volume25
Issue42
Pages (from-to)9856-9860
Number of pages5
ISSN0947-6539
DOIs
Publication statusPublished - Jul 2019

    Research areas

  • alkylzinc reagents, beta-ketonitriles, carbonylation, isotope labeling, nickel catalysis

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