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A New Remote Control for Traceless meta‐CH Olefination of Phenols

The development of a suitable methodology for the introduction of functional groups into the core of aromatic molecules has continued to be an indicator of synthetic progress for over a century. It was already considered of utmost importance nearly 150 years ago, when Kekule dedicated his Chemie der Benzolderivate oder der aromatischen Verbindungen to this particular topic. Within the field of modern arene chemistry, the general concept of direct C H functionalization of arenes represents an area with particularly impressive advances over recent years. Classic concepts rely on suitable directing groups for ortho-functionalization. This concept was widely explored for stoichiometric ortho-lithiation, as well as in more recent developments employing transition metal based catalysts, which rely on cyclometalation reactions, where palladium and ruthenium have played prominent roles. In addition to conventional ortho-functionalization, some groups have recently started to explore the development of suitable catalytic conditions for meta-selective C H derivatization of arenes. Some time ago, Yu described an important break-through in the field of palladium catalysis. By designing suitable directing groups containing nitrile substituents, his group was able to devise an efficient chelation control in order to generate a coordinated palladium complex A and to direct the cyclopalladation to proceed preferentially at the meta-position (Scheme 1).