Combined Directed ortho Metalation−Halogen Dance (HD) Synthetic Strategies. HD−Anionic ortho Fries Rearrangement and Double HD Sequences
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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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MILLER, 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/ol100493vBibTex
@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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