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. 2023 May 31;9(22):eadh3544. doi: 10.1126/sciadv.adh3544

Fig. 5. Effect of light on single-electron transfer from an anion radical of a coupling product.

Fig. 5.

(A) A “light/dark” experiment for the coupling of the phenylzinc reagent with 2-bromonaphthalene (2’s) aided by the BDA photoredox catalysis. (B) Comparison of the action spectrum for the coupling of the phenylzinc reagent with 2-bromonaphthalene (2’s) in the presence of sodium 2-methylnaphthalenide with the absorption spectrum (right axis) of [3as]• – (1.0 × 10−3 M) in THF/DMA (1:1). The yield of the coupling product (3as) (left axis) versus the respective wavelengths of the reaction is shown. The reaction was carried out under photoirradiation (0.30 W). (C) Plausible reaction mechanism. (D) Comparison of the action spectrum for reduction of 4-chloroanisole (1”c) into anisole (4c) with sodium 2-phenylnaphthalenide (Na+ [3as]• –) with the absorption spectrum (right axis) of [3as]• – (1.0 × 10−3 M) in THF/DMA (1:1). The yield of the reduction product (4c) (left axis) versus the respective wavelengths of the reaction is shown. The reaction was carried out under photoirradiation (0.30 W). (E) The effect of the fluorescence of BDA on the coupling of the phenylzinc reagent with 2-bromonaphthalene (2’s) in the presence of sodium 2-methylnaphthalenide. Photos of a 470-nm LED lamp, the fluorescence of BDA excited by a 470-nm LED lamp, the coupling reaction under a BDA photoredox catalysis, and the coupling under the fluorescence of BDA are also put here.