4.7 Article

B(C6F5)3-Catalyzed α,β-Difunctionalization and C-N Bond Cleavage of Saturated Amines with Benzo[c]isoxazoles: Access to Quinoline Derivatives

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 21, Pages 14840-14845

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01290

Keywords

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Funding

  1. National Natural Science Foundation of China
  2. Project of Central Plains Science and Technology Innovation Leading Talents
  3. Program for Innovative Research Team in Science and Technology in Universities of Henan Province
  4. Henan Key Laboratory of Organic Functional Molecules and Drug Innovation
  5. [U2004189]
  6. [224200510009]
  7. [20IRTSTHN005]

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A strategy for a,fi-difunctionalization and C-N bond cleavage of saturated amines with benzo[c]isoxazoles was disclosed, involving B(C6F5)3-catalyzed consecutive hydrogen-borrowing and [4 + 2] cycloaddition followed by a C-N bond cleavage process. The reactions proceed efficiently without the need for oxidants and metal catalysts, providing a broad range of quinoline derivatives in an atom-economical manner.
Herein, we disclose a strategy to realize a,fi-difunctionalization and C-N bond cleavage of saturated amines with benzo[c]isoxazoles via a B(C6F5)3-catalyzed consecutive hydrogen-borrowing and [4 + 2] cycloaddition followed by a C-N bond cleavage process. In general, the reactions proceed efficiently in the absence of any oxidant and metal catalyst to afford a broad range of quinoline derivatives starting from easily accessible substrates in an atom-economical manner.

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