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Reaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki–Miyaura cross-coupling

Author

Listed:
  • Yuqiang Li

    (Wuhan University)

  • Yixin Luo

    (Chongqing University)

  • Long Peng

    (Wuhan University)

  • Yangyang Li

    (Wuhan University)

  • Binzhi Zhao

    (Wuhan University)

  • Wang Wang

    (Wuhan University)

  • Hailiang Pang

    (Wuhan University)

  • Yi Deng

    (Wuhan University)

  • Ruopeng Bai

    (Chongqing University)

  • Yu Lan

    (Chongqing University
    Zhengzhou University)

  • Guoyin Yin

    (Wuhan University)

Abstract

Cross-coupling reactions have developed into powerful approaches for carbon–carbon bond formation. In this work, a Ni-catalyzed migratory Suzuki–Miyaura cross-coupling featuring high benzylic or allylic selectivity has been developed. With this method, unactivated alkyl electrophiles and aryl or vinyl boronic acids can be efficiently transferred to diarylalkane or allylbenzene derivatives under mild conditions. Importantly, unactivated alkyl chlorides can also be successfully used as the coupling partners. To demonstrate the applicability of this method, we showcase that this strategy can serve as a platform for the synthesis of terminal, partially deuterium-labeled molecules from readily accessible starting materials. Experimental studies suggest that migratory cross-coupling products are generated from Ni(0/II) catalytic cycle. Theoretical calculations indicate that the chain-walking occurs at a neutral nickel complex rather than a cationic one. In addition, the original-site cross-coupling products can be obtained by alternating the ligand, wherein the formation of the products has been rationalized by a radical chain process.

Suggested Citation

  • Yuqiang Li & Yixin Luo & Long Peng & Yangyang Li & Binzhi Zhao & Wang Wang & Hailiang Pang & Yi Deng & Ruopeng Bai & Yu Lan & Guoyin Yin, 2020. "Reaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki–Miyaura cross-coupling," Nature Communications, Nature, vol. 11(1), pages 1-13, December.
  • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-019-14016-1
    DOI: 10.1038/s41467-019-14016-1
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    Cited by:

    1. Wan Seok Yoon & Won Jun Jang & Woojin Yoon & Hoseop Yun & Jaesook Yun, 2022. "Copper-catalysed asymmetric reductive cross-coupling of prochiral alkenes," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    2. Ting Wan & Luca Capaldo & Jonas Djossou & Angela Staffa & Felix J. Zwart & Bas Bruin & Timothy Noël, 2024. "Rapid and scalable photocatalytic C(sp2)–C(sp3) Suzuki−Miyaura cross-coupling of aryl bromides with alkyl boranes," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    3. Braulio M. Puerta Lombardi & Morgan R. Faas & Daniel West & Roope A. Suvinen & Heikki M. Tuononen & Roland Roesler, 2024. "An isolable, chelating bis[cyclic (alkyl)(amino)carbene] stabilizes a strongly bent, dicoordinate Ni(0) complex," Nature Communications, Nature, vol. 15(1), pages 1-7, December.

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