4.8 Article

B2pin2-Mediated Cascade Cyclization/Aromatization Reaction: Facial Access to Functionalized Indolizines

Journal

ORGANIC LETTERS
Volume 24, Issue 40, Pages 7372-7377

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02905

Keywords

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Funding

  1. Foundation of Jiangxi Educational Committee
  2. Fundamental Research Funds for Gannan Medical University
  3. National Natural Science Foundation of China
  4. [GJJ211532]
  5. [QD202001]
  6. [21961018]

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This paper describes a B2pin2-mediated radical cascade cyclization/aromatization reaction of enaminone with pyridine, providing a practical way for constructing valuable functionalized indolizines under metal-, external oxidant-, and base-free conditions. The reaction is compatible with various functional groups and is triggered by the in situ formation of a pyridine-boryl radical.
Herein, a B2pin2-mediated radical cascade cyclization/aromatization reaction of enaminone with pyridine is described. This strategy provides a practical way for the construction of valuable functionalized indolizines under metal-, external oxidant-, and base-free conditions, which could be compatible with various kinds of functional groups, such as halogen, pi-system, heterocycle, ferrocenyl, etc. A preliminary mechanism investigation indicated that the pyridine-boryl radical formed in situ triggered the reaction to occur.

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