4.8 Article

Rhodium(III)-Catalyzed Synthesis of Isoquinolines from Aryl Ketone O-Acyloxime Derivatives and Internal Alkynes

Journal

ORGANIC LETTERS
Volume 12, Issue 24, Pages 5688-5691

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol102504b

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Funding

  1. Nanyang Technological University
  2. Singapore Ministry of Education
  3. Science & Engineering Research Council (A*STAR) [082 101 0019]

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A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal allkynes has been developed using [Cp*RhCl2](2) NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C-H vinylation via ortho-rhodation and C-N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N-O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

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