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During the preparation of this manuscript, an interesting aryl azide synthesis, which uses a copper-catalyzed cross-coupling reaction between potassium haloaryltrifluoroborates and sodium azide, was reported as a communication, including the substrate dependent formation of aniline derivatives in a minority of cases (four examples), see: Y. A. Cho, D.-S. Kim, H. R. Ahn, B. Canturk, G. A. Molander, J. Ham. Org. Lett. 2009, 11, 4330-4333.
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see also reference [8] and [17]
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The reaction of aryl halides with secondary amines under transition-metal-free conditions was reported, see: W. Kleist, S.S. Pröckl, M. Drees, K. Köhler, L. Djakovitch, J. Mol. Catal. A 2009, 303, 15-22; see also reference [8] and [17].
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note
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2 in DMA, the mixture turned pale blue. The color change was, presumably, due to the enhanced solubility of copper species caused by the formation of a complex with 2-aminoethanol. The dissolved copper species aids the increase in the reaction efficiency.
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43
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note
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Use of copper plate for the reaction of 4-bromobiphenyl was not effective (36%). Therefore, the morphological properties of the copper metal appear to be important for a smooth reaction.
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44
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note
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No formation of the regioisomers of aminobenzenes was observed, suggesting that the reaction does not proceed via hydroamination of a benzyne intermediate, which might be generated by the removal of hydrogen halide with base in heated polar aprotic solvents.
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