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syn-Selective alkylarylation of terminal alkynes via the combination of photoredox and nickel catalysis

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  • Lei Guo

    (Donghua University)

  • Fan Song

    (Donghua University)

  • Shengqing Zhu

    (Donghua University)

  • Huan Li

    (Donghua University)

  • Lingling Chu

    (Donghua University)

Abstract

Substituted alkenes are pivotal structural motifs found in pharmaceuticals and agrochemicals. Although numerous methods have been developed to construct substituted alkenes, a generally efficient, mild, catalytic platform for the conversion of alkynes to this highly functionalized scaffold via successive C–C bond forming steps remains in high demand. Here we describe an intermolecular, regio- and syn-stereoselective alkylarylation of terminal alkynes with tertiary alkyl oxalates via photoredox-Ni dual catalysis. This catalytic protocol, synergistically combining Ir/Ni-catalyzed alkyne difunctionalization with photoinduced alkene isomerization, affords trisubstituted alkenes with excellent efficiency and syn-stereoselectivity. The mild conditions tolerate many functional groups, allowing for a broad scope with respect to terminal alkynes, aryl bromides, and alkyl oxalates.

Suggested Citation

  • Lei Guo & Fan Song & Shengqing Zhu & Huan Li & Lingling Chu, 2018. "syn-Selective alkylarylation of terminal alkynes via the combination of photoredox and nickel catalysis," Nature Communications, Nature, vol. 9(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-06904-9
    DOI: 10.1038/s41467-018-06904-9
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    Cited by:

    1. Shanglin Chen & Ya-Nan Wang & Jinhui Xie & Wangyang Li & Mingxing Ye & Xingxing Ma & Kai Yang & Shijun Li & Yu Lan & Qiuling Song, 2024. "Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions," Nature Communications, Nature, vol. 15(1), pages 1-14, December.
    2. Shubham Dutta & Shashank Shandilya & Shengwen Yang & Manash Protim Gogoi & Vincent Gandon & Akhila K. Sahoo, 2022. "Cationic-palladium catalyzed regio- and stereoselective syn-1,2-dicarbofunctionalization of unsymmetrical internal alkynes," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    3. Chen Zhu & Huifeng Yue & Magnus Rueping, 2022. "Nickel catalyzed multicomponent stereodivergent synthesis of olefins enabled by electrochemistry, photocatalysis and photo-electrochemistry," Nature Communications, Nature, vol. 13(1), pages 1-9, December.

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