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Synfacts 2010(9): 1058-1058
DOI: 10.1055/s-0030-1257902
DOI: 10.1055/s-0030-1257902
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthetic Strategies of Directed ortho-Metalation and Halogen Dance
R. E. Miller, T. Rantanen, K. A. Ogilvie, U. Groth, V. Snieckus*
Universität Konstanz, Germany and Queen’s University, Kingston, Canada
Further Information
Publication History
Publication Date:
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.