4.8 Article

Super-Electron-Donor 2-Azaallyl Anions Enable Construction of Isoquinolines

Journal

ORGANIC LETTERS
Volume 24, Issue 9, Pages 1786-1790

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00140

Keywords

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Funding

  1. National Key R&D Program of China [2019YFE0109200]
  2. NSFC [U1702286]
  3. Ling-Jun Scholars [202005AB160003]
  4. NSF of Yunnan Province [2019FY003010, 2019FI018]
  5. IRTSTYN
  6. US National Science Foundation [CHE-1902509]

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This study introduces a transition-metal-free method using superelectron-donor for the rapid construction of isoquinolines through a tandem reaction, demonstrating high yields and good functional group tolerance of the method. Additionally, a gram scale synthesis confirms the scalability of the approach.
Herein is introduced the application of superelectron-donor(SED) 2-azaallyl anions in a tandem reduction/radical cyclization/radical coupling/aromatization protocol that enables the rapid construction of isoquinolines. The value of this transition-metal-free method is highlighted by the wide range of isoquinoline ethyl amines prepared with good functional group tolerance and yields. An operationally simple gram scale synthesis is also conducted, confirming the scalability.

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