4.8 Article

Re/Mg Bimetallic Tandem Catalysis for [4+2] Annulation of Benzamides and Alkynes via C-H/N-H Functionalization

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 12, Pages 4628-4631

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja400020e

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Funding

  1. Natural Science Foundation of China [21002103, 21272238]
  2. Major State Basic Research Development Program [2012CB821600]
  3. Institute of Chemistry, CAS

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A rhenium-magnesium cocatalyzed [4+2] annulation of benzamides and alkynes via C-H/N-H functionalization is described. The reaction features a divergent and high level of diastereoselectivities, which are readily switchable by subtle tuning of reaction conditions. Thus, a wide range of both cis- and trans-3,4-dihydroisoquinolinones is expediently synthesized in a highly atom-economical manner. Moreover, mechanistic studies unraveled a tandem mode of action between rhenium and magnesium in the catalytic cycles.

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