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Nickel catalyzed multicomponent stereodivergent synthesis of olefins enabled by electrochemistry, photocatalysis and photo-electrochemistry

Author

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  • Chen Zhu

    (King Abdullah University of Science and Technology (KAUST))

  • Huifeng Yue

    (King Abdullah University of Science and Technology (KAUST))

  • Magnus Rueping

    (King Abdullah University of Science and Technology (KAUST)
    RWTH Aachen University)

Abstract

Trisubstituted alkenes are important organic synthons and have broad applications in the synthesis of many pharmaceuticals and materials. The stereoselective synthesis of such compounds has long been a research focus for organic researchers. Herein, we report a three-component, reductive cascade, cross-coupling reaction for the arylalkylation of alkynes. A wide range of trisubstituted alkenes are obtained in good to high yields with excellent chemo- and stereoselectivity by switching between electrochemistry and photocatalysis. The E isomer of the product is obtained exclusively when the reaction is conducted with electricity and nickel, while the Z isomer is generated with high stereoselectivity when photo- and nickel dual catalysts are used. Moreover, photo-assisted electrochemically enabled nickel catalyzed protocol is demonstrated to selectively deliver Z-trisubstituted alkenes without the addition of photocatalysts.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30985-2
    DOI: 10.1038/s41467-022-30985-2
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    References listed on IDEAS

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    1. Thach T. Nguyen & Ming Joo Koh & Tyler J. Mann & Richard R. Schrock & Amir H. Hoveyda, 2017. "Synthesis of E- and Z-trisubstituted alkenes by catalytic cross-metathesis," Nature, Nature, vol. 552(7685), pages 347-354, December.
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    3. Jinbao Xiang & Ming Shang & Yu Kawamata & Helena Lundberg & Solomon H. Reisberg & Miao Chen & Pavel Mykhailiuk & Gregory Beutner & Michael R. Collins & Alyn Davies & Matthew Bel & Gary M. Gallego & Ji, 2019. "Hindered dialkyl ether synthesis with electrogenerated carbocations," Nature, Nature, vol. 573(7774), pages 398-402, September.
    4. Han Wang & Ren Wei Toh & Xiangcheng Shi & Tonglin Wang & Xu Cong & Jie Wu, 2020. "Photo-mediated selective deconstructive geminal dihalogenation of trisubstituted alkenes," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    5. 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.
    6. Long Huang & Tengfei Ji & Chen Zhu & Huifeng Yue & Nursaya Zhumabay & Magnus Rueping, 2022. "Bioinspired desaturation of alcohols enabled by photoredox proton-coupled electron transfer and cobalt dual catalysis," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
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    1. Jinghao Wang & Siyang Li & Caoyu Yang & Huiwen Gao & Lulu Zuo & Zhiyu Guo & Pengqi Yang & Yuheng Jiang & Jian Li & Li-Zhu Wu & Zhiyong Tang, 2024. "Photoelectrochemical Ni-catalyzed cross-coupling of aryl bromides with amine at ultra-low potential," Nature Communications, Nature, vol. 15(1), pages 1-8, December.

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