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

Abstract
An efficient iodination reaction of electron-deficient heterocycles is described. The reaction utilizes KOtBu as an initiator and likely proceeds by a radical anion propagation mechanism. This new methodology is particularly effective for functionalization of building blocks for electron transport materials. Its utility is demonstrated with the synthesis of a new perylenediimide-thiazole non-fullerene acceptor capable of delivering a power conversion efficiency of 4.5% in a bulk-heterojunction organic solar cell. © 2016 American Chemical Society.

Citation
Shi Q, Zhang S, Zhang J, Oswald VF, Amassian A, et al. (2016) KO t Bu-Initiated Aryl C–H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds . Journal of the American Chemical Society 138: 3946–3949. Available: http://dx.doi.org/10.1021/jacs.5b12259.

Acknowledgements
This research was supported by the National Science Foundation under the Center for Chemical Innovation in Selective C-H Functionalization (CHE-1205646) and the MRSEC Program (DMR-0820382). The authors thank Professor A. S. Borovik for helpful discussions regarding EPR spectroscopy, Dr. Anil Mehta and the Emory University Solid State NMR Research Center for assistance with solid-state NMR spectroscopy, and Dr. John Bacsa and Marika Wieliczko (Emory X-ray Center) for X-ray structural analysis.

Publisher
American Chemical Society (ACS)

Journal
Journal of the American Chemical Society

DOI
10.1021/jacs.5b12259

PubMed ID
26996823

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