Synfacts 2010(9): 1058-1058  
DOI: 10.1055/s-0030-1257902
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Strategies of Directed ortho-Metalation and Halogen Dance

Contributor(s): Paul Knochel, Thomas Kunz
R. E. Miller, T. Rantanen, K. A. Ogilvie, U. Groth, V. Snieckus*
Universität Konstanz, Germany and Queen’s University, Kingston, Canada
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Publikationsverlauf

Publikationsdatum:
23. August 2010 (online)

Significance

An efficient directed ortho-metalation-halogen dance sequence for the synthesis of trisubstituted pyridyl O-carbamates is reported. A subsequent halogen dance sequence affords tetrasubstituted pyridines. Moreover, after metalation and halogen dance an anionic ortho-Fries rearrangement is observed on substituted aromatic O-carbamates.