4.6 Article

A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 29, Pages 7924-7927

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob01222h

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Funding

  1. Soochow University
  2. National Natural Science Foundation of China [21402134]
  3. Natural Science Foundation of Jiangsu [BK20140306]
  4. Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
  5. Natural Science Foundation of China [NSFC 21302133]

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A regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion is described. A variety of 1-tetralones are furnished under mild reaction conditions from tertiary cyclobutanols regardless of the electronic properties and steric hindrance of substituents, providing a new and practical method to access diverse 1-tetralone building blocks. Preliminary experimental and DFT studies revealed that a radical-mediated sequence of C-C bond cleavage/C-C bond formation is involved.

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