4.7 Article

Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 22, Pages 11388-11397

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01962

Keywords

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Funding

  1. National Science Foundation [CHE1265964]
  2. National Institute of General Medical Sciences [R01-GM098601]
  3. Alexander von Humboldt Foundation
  4. NIH
  5. Direct For Mathematical & Physical Scien [1265964] Funding Source: National Science Foundation
  6. Division Of Chemistry [1265964] Funding Source: National Science Foundation

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Visible-light photoreductive coupling of 2-arylallyl bromides in the presence of the photocatalyst Ru(bpy)(3)(PF6)(2), a Hantzsch ester, and i-Pr2NEt gives 2,5-diaryl-1,5-dienes in high yield. This method avoids the use of stoichiometric metal reductants and is compatible with the presence of halogen, alkyl, electron-donating, and electron-withdrawing substituents on the aromatic ring.

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