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Photochemistry

Strongly reducing Ir photoredox on aryl chlorides

Shon JH, Kim D, Rathnayake MD, et al. · Chemical science · 2021

Open access · cc by · source: Europe PMC

Ir(ppy)2(NacNac) photocatalysts with BIH hydrodehalogenate unactivated aryl bromides, chlorides, fluorides, and alkyl bromides, including with green light.

Key findings

Excited-state potentials are −2.6 V (Ir1) and −2.4 V (Ir2) vs Fc+/Fc, ~300–500 mV more reducing than fac-Ir(ppy)3. With 1 mol% Ir and BIH, aryl bromides work in 24 h; aryl chlorides give quantitative yields with Ir1/blue light. Quantum yields are 4.7% (S2) and 1.4% (S7). Light/dark cycling shows catalysis needs light.

Methodology

They used two β-diketiminate iridium complexes (Ir1, Ir2) plus 1,3-dimethyl-2-phenylbenzimidazoline (BIH) under blue or green LEDs. Scope included hydrodebromination, hydrodechlorination, alkyl bromides, radical cyclization, and ether C–O cleavage. Quantum yields and Stern–Volmer quenching rates were measured.

Limitations

Quantum yields <100% do not fully exclude short radical chains. Many reactions were set up in a glovebox; ambient stability of stock solutions is limited. Isolated-yield tables for every substrate are not all in the main text.

How this study connects

Role on claims

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  • SupportsPhotochemistryconcept

    This library holds 10 empirical chemistry papers on photochemistry with isolated findings, rates or spectra rather than reviews.

    Evidence for the claim as stated.

  • SupportsPhotochemistryconcept

    Ir(ppy)2(NacNac) photocatalysts with BIH hydrodehalogenate unactivated aryl bromides, chlorides, fluorides, and alkyl bromides, including with green light.

    Evidence for the claim as stated.

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