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Harnessing Photocatalytic Single-Electron Oxidation: Radical Precursors for Efficient Metallaphotoredox Couping Reactions

17 January 2025

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In the past decade, metal polypyridyl complexes have emerged as powerful photoredox catalysts that, upon excitation by visible light, engage in single-electron transfer (SET) with common functional groups. This process activates nontraditional sites of reactivity on standard substrates via low-barrier, open-shell processes, thereby enabling the use of abundant and inexpensive starting materials.

Transition metal catalysis has long been a robust strategy for constructing complex molecules from simple, readily accessible starting materials. However, it often requires a stoichiometric oxidant or reductant to adjust the oxidation state of the metal catalyst. To address this challenge, the groups of MacMillan and Molander combined the SET process of photoredox catalysis with nickel-catalyzed radical alkylation of aryl halides. These redox-neutral metallaphotoredox processes utilize carboxylic acids and alkylboron derivatives as radical precursors.

In these processes, the radical precursors are single-electron oxidized by the excited photocatalyst to form a radical. Simultaneously, the Ni(0) precatalyst undergoes oxidative addition to the aryl halides. The resulting Ni(II) complex then captures the radical, forming a Ni(III) species. This species subsequently undergoes reductive elimination, yielding the corresponding alkylation product along with a Ni(I) species, which is then further single-electron reduced by the photoredox catalytic system back to the Ni(0) precatalyst.

Given the success of these metallaphotoredox systems, the demand for reliable and efficient radical precursors has grown significantly. In response, we are excited to offer a selection of high-quality, ready-to-use radical precursors designed to generate radicals through single-electron oxidation for use in photoredox catalysis. Our range includes carboxylic acids, alkylboron derivatives, 1,4-dihydropyridines, sodium sulfonate, α-trimethylsilylamines, α-keto acids and other radical precursors commonly utilized in photoredox processes. These precursors are meticulously synthesized and tested to ensure both purity and effectiveness in facilitating efficient radical generation under photochemical conditions.

References

[1]Science 2014, 345, 433.

[2]Science 2014, 345, 437.

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