4.6 Article

Nickel-Catalyzed Tandem Reaction of Functionalized Arylacetonitriles with Arylboronic Acids in 2-MeTHF: Eco-Friendly Synthesis of Aminoisoquinolines and Isoquinolones

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 15, Issue 1, Pages 106-111

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201901442

Keywords

2-MeTHF; Aminoisoquinolines; Arylacetonitriles; Isoquinolones; Nickel

Funding

  1. National Natural Science Foundation of China [21572162]
  2. Natural Science Foundation of Zhejiang Province [LY20B020015, LQ18B020006]

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The first example of the nickel-catalyzed tandem addition/cyclization of 2-(cyanomethyl)benzonitriles with arylboronic acids in 2-MeTHF has been developed, which provides the facile synthesis of aminoisoquinolines with good functional group tolerance under mild conditions. This chemistry has also been successfully applied to the synthesis of isoquinolones by the tandem reaction of methyl 2-(cyanomethyl)benzoates with arylboronic acids. The use of the bio-based and green solvent 2-MeTHF as the reaction medium makes the synthesis process environmentally benign. The synthetic utility of this chemistry is also indicated by the synthesis of biologically active molecules.

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