Intermolecular oxidative dehydrogenative 3,3′-coupling of benzo[b]furans and benzo[b]thiophenes promoted by DDQ/H+: total synthesis of shandougenine B

@article{Wirtanen2016IntermolecularOD,
  title={Intermolecular oxidative dehydrogenative 3,3′-coupling of benzo[b]furans and benzo[b]thiophenes promoted by DDQ/H+: total synthesis of shandougenine B},
  author={Tom Wirtanen and Mikko Muuronen and Juha Hurmalainen and H. Tuononen and M. Nieger and Juho Helaja},
  journal={Organic chemistry frontiers},
  year={2016},
  volume={3},
  pages={1738-1745}
}
  • Tom Wirtanen, Mikko Muuronen, +3 authors Juho Helaja
  • Published 2016
  • Chemistry
  • Organic chemistry frontiers
    • With an excess of a strong acid, 2,3-dichloro-5,6-dicyano-1,4-quinone (DDQ) is shown to promote metal-free intermolecular oxidative dehydrogenative (ODH) 3,3′-coupling of 2-aryl-benzo[b]furans and 2-aryl-benzo[b]thiophenes up to 92% yield as demonstrated with 9 substrates. Based on the analysis of oxidation potentials and molecular orbitals combined with EPR, NMR and UV-Vis observations, the studied reaction is initiated by a DDQ-substrate charge transfer complex and presumably proceeds via… CONTINUE READING
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