The photo-induced electron transfer from sacrificial donor amines to aryl bromides generates highly reactive aryl radical intermediates that are useful in a wide variety of photoredox cross coupling reactions. We present a novel approach to “online” high throughput screening (HTS) to evaluate photocatalysts’ (PCs) performance in such reactions (Figure). Cationic iridium complexes [Ir(CN)<sub>2</sub>(NN)]<sup>+</sup> are perfectly suited for combinatorial screening of such transformations because of their modular ligand arrangement and charge transfer excited state. Judicious design of the cyclometalating (CN) and ancillary (NN) ligands results in structurally very diverse PCs with a wide range of photophysical and chemical properties. We developed an indicator dye-based colorimetric technique that allowed us to measure the reaction rate of over a thousand debromination reactions on aryl halides substrates using libraries of such PCs. The discovered structure-activity relationships revealed that the careful choice of PC and sacrificial electron donor can help pinpointing desirable chemoselective and rapid reaction conditions.

High-throughput kinetics screening of iridium catalyzed photo-dehalogenation of aryl bromines

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.