4.8 Article

Combining photochemistry and catalysis: rapid access to sp(3) - rich polyheterocycles from simple pyrroles

Journal

CHEMICAL SCIENCE
Volume 7, Issue 3, Pages 2302-2307

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc04062k

Keywords

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Funding

  1. EPSRC Bristol Chemical Synthesis Doctoral Training Centre [EP/G036764/1]
  2. University of Bristol
  3. EPSRC [EP/L003325/1, EP/K006053/1, EP/K03927X/1] Funding Source: UKRI
  4. Engineering and Physical Sciences Research Council [EP/L003325/1, EP/K03927X/1, EP/K006053/1] Funding Source: researchfish

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Use of FEP flow reactor technology allows access to gram quantities of photochemically-generated tricyclic aziridines. These undergo a range of novel palladium-catalyzed ring-opening and cycloaddition reactions, likely driven by their inherent strain, allowing incorporation of further functionality by fusing additional heterocyclic rings onto these already complex polycyclic cores. This rapid, 2-step access to complex sp(3) - rich heterocycles should be of interest to those in the fields of drug discovery and natural product synthesis.

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