4.8 Article

Nickel-Catalyzed β-Regioselective Amination/Cyclization of Ynamide-Nitriles with Amines: Synthesis of Functionalized 3-Aminoindoles and 4-Aminoisoquinolines

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ORGANIC LETTERS
卷 23, 期 4, 页码 1296-1301

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c04278

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资金

  1. National Key R&D Program of China [2016YFA0202900]
  2. National Natural Science Foundation of China [21772217]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  4. Science and Technology Commission of Shanghai Municipality [18XD1405000]

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A highly regioselective nickel/Lewis acid catalyzed amination/cyclization reaction of ynamide-nitriles with amines involving beta-addition has been developed, providing an efficient route for the synthesis of 3-aminoindoles and 4-aminoisoquinoline derivatives. The Ts-group on the ynamide serves as a directing group, leading to the formation of alkenyl nickel species with high regioselectivity.
A highly regioselective nickel/Lewis acid catalyzed amination/cyclization of ynamide-nitriles with amines involving beta-addition has been developed. The reaction offers an attractive and efficient route for the synthesis of 3-aminoindoles and 4-aminoisoquinoline derivatives. The Ts-group on the ynamide acts as a directing group to produce the alkenyl nickel species with high regioselectivity.

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