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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)


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Abstract

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.

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Key Words

Directed Ortho Metalation, Carbamates


ID: J54-Y2010-1900