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Photoinduced Ullmann C–N Coupling: Demonstrating the Viability of a Radical Pathway

Science  02 Nov 2012:
Vol. 338, Issue 6107, pp. 647-651
DOI: 10.1126/science.1226458

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Abstract

Carbon–nitrogen (C–N) bond-forming reactions of amines with aryl halides to generate arylamines (anilines), mediated by a stoichiometric copper reagent at elevated temperature (>180°C), were first described by Ullmann in 1903. In the intervening century, this and related C–N bond-forming processes have emerged as powerful tools for organic synthesis. Here, we report that Ullmann C–N coupling can be photoinduced by using a stoichiometric or a catalytic amount of copper, which enables the reaction to proceed under unusually mild conditions (room temperature or even –40°C). An array of data are consistent with a single-electron transfer mechanism, representing the most substantial experimental support to date for the viability of this pathway for Ullmann C–N couplings.

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