4.7 Article

Catalytic Synthesis of Luminescent Pyrimidines via Acceptor-less Dehydrogenative Coupling

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 21, Pages 13747-13756

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01882

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Funding

  1. Natural Sciences Engineering Research Council of Canada [RGPIN-2014-03733]
  2. Canadian Foundation for Innovation and Research Manitoba [32146]
  3. University of Manitoba
  4. Mitacs
  5. Compute Canada

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A simple catalytic synthesis of luminescent pyrimidines from benzamidines and alcohols is reported. These one-pot, acceptor-less dehydrogenative coupling reactions are catalyzed by a ruthenium hydrido chloride complex (1), supported by a chelating PAN ligand (L1) bearing a benzannulated phenanthridine donor arm. The pyrimidines thus produced are emissive in solution, with photoluminescence quantum yields reaching 72%. Details of the catalytic synthesis and characterization of the pyrimidines in both solution and the solid state are reported, along with computational modeling of the emissive excited states of representative examples.

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