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Synfacts 2010(8): 0936-0936  
DOI: 10.1055/s-0030-1257758
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Phosphorodiamidate-Directed Metalation of N-Heterocycles using Mg- and Zn-TMP

Contributor(s): Paul Knochel, Andreas J. Wagner
C. J. Rohbogner, S. Wirth, P. Knochel*
Ludwig-Maximilians-Universität München, Germany
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

The strong metalation-directing power of the tetramethylphosphorodiamidate group has been used for achieving selective metalations on various N-heterocycles like pyridines, quinolines, and quinoxalines using TMP-derived bases. The resulting ortho-metalated species can be trapped with a wide range of electrophiles ­affording functionalized heteroaromatics in very good yields.