4.8 Article

Redox-Divergent Hydrogen-Retentive or Hydrogen-Releasing Synthesis of 3,4-Dihydroisoquinolines or Isoquinolines

Journal

ORGANIC LETTERS
Volume 18, Issue 12, Pages 2840-2843

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01091

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Funding

  1. Xi'an Jiaotong University
  2. NSFC [21472145]

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A rare Ru-catalyzed highly selective synthesis of: 3,4-dihydroisoquiuolines or isoquinolines is accomplished via a redox-divergent hydrogen-retentive or, hydrogen-releasing fashion. Notably, high cis-selectivity of 3,4-dihydroisoquino lines is achieved. Potential applications, are shown by gram,: scale reactions and very concise synthesis of N-containing polycyclic aromatic compounds. Primary mechanistic investigations indicate that the sequence of the major pathway involves Ru-catalyzed C-H activation, alkyne insertion, and subsequent 6 pi-electrocyclization.

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