Combined Directed ortho Metalation−Halogen Dance (HD) Synthetic Strategies. HD−Anionic ortho Fries Rearrangement and Double HD Sequences

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2010
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Rantanen, Toni
Ogilvie, Kevin A.
Snieckus, Victor
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Organic Letters. 2010, 12(10), pp. 2198-2201. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/ol100493v
Zusammenfassung

A general and efficient directed ortho metalation (DoM)−halogen dance (HD)−electrophile quench sequence for the synthesis of trisubstituted pyridyl O-carbamates is described. A second HD sequence furnishes highly functionalized tetrasubstituted pyridines. Furthermore, a hitherto unobserved double HD rearrangement is reported. Under similar LDA conditions, aromatic O-carbamates with OMe, Cl, and F substituents (4a−c) undergo either a HD−electrophile quench sequence, 4a−c → 18−20, or a HD−anionic ortho Fries rearrangement, 4a−c → 6a−c, respectively.

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ISO 690MILLER, Ricarda, Toni RANTANEN, Kevin A. OGILVIE, Ulrich GROTH, Victor SNIECKUS, 2010. Combined Directed ortho Metalation−Halogen Dance (HD) Synthetic Strategies. HD−Anionic ortho Fries Rearrangement and Double HD Sequences. In: Organic Letters. 2010, 12(10), pp. 2198-2201. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/ol100493v
BibTex
@article{Miller2010Combi-12586,
  year={2010},
  doi={10.1021/ol100493v},
  title={Combined Directed ortho Metalation−Halogen Dance (HD) Synthetic Strategies. HD−Anionic ortho Fries Rearrangement and Double HD Sequences},
  number={10},
  volume={12},
  issn={1523-7060},
  journal={Organic Letters},
  pages={2198--2201},
  author={Miller, Ricarda and Rantanen, Toni and Ogilvie, Kevin A. and Groth, Ulrich and Snieckus, Victor}
}
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