Facile Double-Lithiation of a Transient Urea: Vicarious ortho-Metalation of Aniline Derivatives
Chris E. Houlden, Guy C. Lloyd-Jones* and Kevin I. Booker-Milburn*
*School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, U.K., Email: k.booker-milburnbristol.ac.uk, guy.lloyd-jonesbris.ac.uk
C. E. Houlden, G. C. Lloyd-Jones, K. I. Brooker-Milburn, Org. Lett., 2010, 12, 3090-3092.
DOI: 10.1021/ol101102y (free Supporting Information)
see article for more reactions
A convenient one-pot method allows the conversion of phenylisocyanate into ortho-functionalized aniline derivatives. The reaction proceeds via a selective ortho-metalation of a transient labile urea, which can be considered as a synthetic equivalent of 2-lithio-phenylisocyanate, a highly improbable intermediate.
see article for more examples