KOtBu-Initiated Aryl C–H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds

Qinqin Shi, Siyuan Zhang, Junxiang Zhang, Victoria F. Oswald, Aram Amassian, Seth R. Marder, and Simon B. Blakey

J. Am. Chem. Soc.,
2016, 138 (12), pp 3946–3949; 10.1021/jacs.5b12259


Cross-Coupling technology has transformed the way that organic molecules are put together, impacting the field broadly, but particularly in the pharmaceutical and material sciences. A key shortfall in this field is the dearth of effective methods to introduce the functional groups required for cross-coupling into electron-poor structural motifs. These electron-deficient molecules are critical components optically and electronically active materials.

This collaborative study from the Blakey, Marder and Amassian groups describes the science behind taking a fortuitous observation of a side-product, through the development and optimization of a novel technique for the functionalization of electron-poor aromatic systems all the way to the application of materials synthesized using this technology in an Organic Photovoltatic device (OPV).

This new iodination approach, catalyzed by the earth abundant element potassium, provides the means to functionalize molecules that do not react under the established conditions. The reaction is applicable across a broad range of electron deficient heterocycles and aromatics, underlining the significance of this transformation, not just for the materials field, but also for its application in the synthesis of drug-like molecules.

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