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Synfacts 2008(6): 0626-0626  
DOI: 10.1055/s-2008-1072783
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Anionic N-Fries Rearrangement Induced by I-Mg Exchange

Contributor(s): Paul Knochel, Tobias Thaler
F. Ding, Y. Zhang, B. Qu, G. Li, V. Farina, B. Z. Lu*, C. H. Senanayake
Boehringer Ingelheim Pharmaceuticals, Ridgefield, USA
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Publication History

Publication Date:
21 May 2008 (online)

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Significance

This article presents an expedient one-pot process for the easy preparation of oxo-anilides, via an iodine-magnesium exchange, regiospecific anionic ortho-N-Fries rearrangement and in situ trapping of the aniline anion. The oxo-anilides can subsequently be subjected to McMurry cyclization reactions, thus offering a convenient access to 1,2,3-trisubstituted indoles with tertiary carbon substituents at the C3 position.