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A visible-light activated secondary phosphine oxide ligand enabling Pd-catalyzed radical cross-couplings

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  • Takahito Kuribara

    (Chiba University)

  • Masaya Nakajima

    (Chiba University)

  • Tetsuhiro Nemoto

    (Chiba University)

Abstract

Although transition metal-catalyzed reactions have evolved with ligand development, ligand design for palladium-catalyzed photoreactions remains less explored. Here, we report a secondary phosphine oxide ligand bearing a visible-light sensitization moiety and apply it to Pd-catalyzed radical cross-coupling reactions. The tautomeric phosphinous acid coordinates to palladium in situ, allowing for pseudo-intramolecular single-electron transfer between the ligand and palladium. Molecular design of the metal complexes aided by time-dependent density functional theory calculations enables the involvement of allyl radicals from π-allyl palladium(II) complexes, and alkyl and aryl radicals from the corresponding halides and palladium(0) complex. This complex enables radical cross-couplings by ligand-to-Pd(II) and Pd(0)-to-ligand single-electron transfer under visible-light irradiation.

Suggested Citation

  • Takahito Kuribara & Masaya Nakajima & Tetsuhiro Nemoto, 2022. "A visible-light activated secondary phosphine oxide ligand enabling Pd-catalyzed radical cross-couplings," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31613-9
    DOI: 10.1038/s41467-022-31613-9
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    References listed on IDEAS

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    1. Kohsuke Ohmatsu & Tsubasa Nakashima & Makoto Sato & Takashi Ooi, 2019. "Direct allylic C–H alkylation of enol silyl ethers enabled by photoredox–Brønsted base hybrid catalysis," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
    2. Geun Seok Lee & Daeun Kim & Soon Hyeok Hong, 2021. "Pd-catalyzed formal Mizoroki–Heck coupling of unactivated alkyl chlorides," Nature Communications, Nature, vol. 12(1), pages 1-12, December.
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