An efficient organocatalytic method for constructing biaryls through aromatic C–H activation

Abstract

The direct functionalization of C–H bonds has drawn the attention of chemists for almost a century. C–H activation has mainly been achieved through four metal-mediated pathways: oxidative addition, electrophilic substitution, σ-bond metathesis and metal-associated carbene/nitrene/oxo insertion. However, the identification of methods that do not require transition-metal catalysts is important because methods involving such catalysts are often expensive. Another advantage would be that the requirement to remove metallic impurities from products could be avoided, an important issue in the synthesis of pharmaceutical compounds. Here, we describe the identification of a cross-coupling between aryl iodides/bromides and the C–H bonds of arenes that is mediated solely by the presence of 1,10-phenanthroline as catalyst in the presence of KOt-Bu as a base. This apparently transition-metal-free process provides a new strategy with which to achieve direct C–H functionalization. C–H activation has usually been achieved by transition metal-mediated pathways. Here, a cross-coupling between aryl halides and common arenes mediated by 1,10-phenanthroline as catalyst, in the presence of potassium tert-butoxide as base is described. Such reactions open a new window for achieving C–H activation without the need for transition metal catalysts.

Cite this article

Sun, CL., Li, H., Yu, DG. et al. An efficient organocatalytic method for constructing biaryls through aromatic C–H activation. Nature Chem 2, 1044–1049 (2010). https://doi.org/10.1038/nchem.862

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