Transient Urea as Directing Group: Synthesis of ortho-Functionalized Anilines

C. E. Houlden; G. C. Lloyd-Jones; K. I. Booker-Milburn

doi:10.1055/s-0030-1258603

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Synfacts 2010(10): 1174-1174
DOI: 10.1055/s-0030-1258603

Metal-Mediated Synthesis

Transient Urea as Directing Group: Synthesis of ortho-Functionalized Anilines

Contributor(s): Paul Knochel, Thomas Kunz
C. E. Houlden, G. C. Lloyd-Jones*, K. I. Booker-Milburn*
University of Bristol, UK

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Publication History

Publication Date:
22 September 2010 (online)

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Significance

This work discloses a one-pot procedure for the synthesis of ortho-functionalized aniline derivatives. The conversion of the arylisocyanate substrates proceeds via the selective ortho-metalation of a labile urea intermediate, which sequentially reacts with a wide range of electrophiles and nucleophiles.